Advances in Bifunctional Squaramide-Catalyzed Asymmetric Sulfa-Michael Addition: A Decade Update

Steeva Sunny; Mohit Maingle; Kapileswar Seth

doi:10.1055/a-1921-0748

Synlett, Table of Contents

Synlett 2023; 34(06): 572-600
DOI: 10.1055/a-1921-0748

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Chemical Synthesis and Catalysis in India

Advances in Bifunctional Squaramide-Catalyzed Asymmetric Sulfa-Michael Addition: A Decade Update

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Abstract

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Abstract

The application of bifunctional organocatalysts in organic chemistry has advanced remarkably owing to their high stability to moisture and air, relatively low toxicity, ease of handling, and recoverability. Among chiral bifunctional organocatalysts, squaramides have emerged as a privileged catalyst in recent years. This review article presents a comprehensive report on fine-tunable bifunctional chiral squaramide-catalyzed sulfa-Michael addition, which is based upon synchronous interplay of synergistic ‘electrophilic–nucleophilic’ dual activation strategies via multiple H-bonding interactions for the construction of both common and complex molecular entities bearing multiple stereocenters. Mechanistic discussions are kept brief, but significant understandings have been recorded. The contribution of squaramide catalyst to the construction of C–S bonds via sulfa-Michael addition has been applied in medicinal, natural, and industrial chemistry. Attention is focused on summarizing the progress made in chiral squaramide-catalyzed asymmetric sulfa-Michael addition and subsequent cascade/domino reaction sequences between 2011 and 2022.

1 Introduction

2 Quinine-Squaramide Organocatalysis

3 Iminophosphorane-Squaramide Organocatalysis

4 Chinchona-Squaramide Organocatalysis

5 trans-1,2-Diaminocyclohexane-Squaramide Organocatalysis

6 Conclusion

Key words

organocatalyst - sulfa-Michael addition - bifunctional chiral squaramide - H-bonding - stereoselectivity

Full Text

References

References

Selected recent reviews:

1a Xiang S.-H, Tan B. Nat. Commun. 2020; 11: 3786
1b Chauhan P, Mahajan S, Enders D. Chem. Rev. 2014; 114: 8807
1c Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev. 2014; 114: 9047
1d Shirakawa S, Maruoka K. Angew. Chem. Int. Ed. 2013; 52: 4312
1e Jensen KL, Dickmeiss G, Jiang H, Albrecht Ł, Jørgensen KA. Acc. Chem. Res. 2012; 45: 248
1f Akiyama T. Chem. Rev. 2007; 107: 5744
1g Doyle AG, Jacobsen EN. Chem. Rev. 2007; 107: 5713
1h Mukherjee S, Yang JW, Hoffmann S, List B. Chem. Rev. 2007; 107: 5471
1i List B. Chem. Rev. 2007; 107: 5413
1j Taylor MS, Jacobsen EN. Angew. Chem. Int. Ed. 2006; 45: 1520

Selected examples:

2a Han B, He X.-H, Liu Y.-Q, He G, Peng C, Li J.-L. Chem. Soc. Rev. 2021; 50: 1522
2b Rai P, Sagir H, Kumar A, Yadav VB, Siddiqui IR. ChemistrySelect 2018; 3: 2565
2c Grondal C, Jeanty M, Enders D. Nat. Chem. 2010; 2: 167
2d Nising CF, Bräse S. Chem. Soc. Rev. 2008; 37: 1218
2e de Figueiredo RM, Christmann M. Eur. J. Org. Chem. 2007; 2575
2f Kotke M, Schreiner PR. Synthesis 2007; 779
2g Suri JT, Steiner DD, Barbas CF. III. Org. Lett. 2005; 7: 3885
2h Schreiner PR. Chem. Soc. Rev. 2003; 32: 289

3a Zhou H, Zhou Y, Bae HY, Leutzsch M, Li Y, De CK, Cheng G.-J, List B. Nature 2022; 605: 84
3b McMillan DW. C. Nature 2008; 455: 304
3c Dondoni A, Massi A. Angew. Chem. Int. Ed. 2008; 47: 4638
3d Pellissier H. Tetrahedron 2007; 63: 9267
3e Dalko PI, Moisan L. Angew. Chem. Int. Ed. 2004; 43: 5138
3f Halland N, Hansen T, Jørgensen KA. Angew. Chem. Int. Ed. 2003; 42: 4955

Selected recent examples:

4a Guo F, Chen J, Huang Y. ACS Catal. 2021; 11: 6316
4b Sharma P, Gupta R, Bansal RK. Beilstein J. Org. Chem. 2021; 17: 2585
4c Phelan JP, Ellman JA. Beilstein J. Org. Chem. 2016; 12: 1203
4d Cho B, Wong MW. Molecules 2015; 20: 15108
4e Yu Z, Liu X, Zhou L, Lin L, Feng X. Angew. Chem. Int. Ed. 2009; 48: 5195

5 Enders D, Lüttgen K, Narine AA. Synthesis 2007; 959
6 Malerich JP, Hagihara K, Rawal VH. J. Am. Chem. Soc. 2008; 130: 14416

7a Ni X, Li X, Wang Z, Cheng J.-P. Org. Lett. 2014; 16: 1786
7b Storer RI, Aciro C, Jones LH. Chem. Soc. Rev. 2011; 40: 2330
7c Quiñonero D, Prohens R, Garau C, Frontera A, Ballester P, Costa A, Deyá PM. Chem. Phys. Lett. 2002; 351: 115
7d Tomàs S, Prohens R, Vega M, Rotger MC, Deyá PM, Ballester P, Costa A. J. Org. Chem. 1996; 61: 9394

8 Cohen S, Cohen SG. J. Am. Chem. Soc. 1966; 88: 1533

Selected recent examples of Michael addition:

9a Kucherenko AS, Kostenko AA, Komogortsev AN, Lichitsky BV, Fedotov MY, Zlotin SG. J. Org. Chem. 2019; 84: 4304
9b Zhao M.-X, Zhu G.-Y, Zhao X.-L, Shi M. Tetrahedron 2019; 75: 1171
9c Yang Z.-T, Zhao J, Yang W.-L, Deng W.-P. Org. Lett. 2019; 21: 1015
9d Chhanda SA, Itsuno S. J. Catal. 2019; 377: 543
9e Li X, Wang Z, Sun J, Gao J, Zhao Y, Cheng P, Aguila B, Ma S, Chen Y, Zhang Z. Chem. Commun. 2019; 55: 5423
9f Valle M, Martín L, Maestro A, Andrés JM, Pedrosa R. Polymers 2019; 11: 13
9g Kisszekelyi P, Alammar A, Kupai J, Huszthy P, Barabas J, Holtzl T, Szente L, Bawn C, Adams R, Szekely G. J. Catal. 2019; 371: 255
9h Kostenko AA, Kucherenko AS, Komogortsev AN, Lichitsky BV, Zlotin SG. Org. Biomol. Chem. 2018; 16: 9314
9i Grayson MN. J. Org. Chem. 2017; 82: 4396
9j Zhang X.-L, Tang C.-K, Xia A.-B, Feng K.-X, Du X.-H, Xu D.-Q. Eur. J. Org. Chem. 2017; 3152
9k Kaya U, Chauhan P, Hack D, Deckers K, Puttreddy R, Rissanen K, Enders D. Chem. Commun. 2016; 52: 1669
9l Zhao M.-X, Zhu H.-K, Dai T.-L, Shi M. J. Org. Chem. 2015; 80: 11330
9m Bera K, Namboothiri IN. N. Org. Biomol. Chem. 2014; 12: 6425
9n Zhong Y, Ma S, Xu Z, Chang M, Wang R. RSC Adv. 2014; 4: 49930
9o Zhou E, Liu B, Dong C. Tetrahedron: Asymmetry 2014; 25: 181
9p Bera K, Namboothiri IN. N. Chem. Commun. 2013; 49: 10632
9q Yang KS, Nibbs AE, Türkmen YE, Rawal VH. J. Am. Chem. Soc. 2013; 135: 16050
9r Kasaplar P, Rodríguez-Escrich C, Pericàs MA. Org. Lett. 2013; 15: 3498
9s Kardos G, Soós T. Eur. J. Org. Chem. 2013; 4490
9t Baran R, Veverková E, Škvorcová A, Šebesta R. Org. Biomol. Chem. 2013; 11: 7705
9u Li J.-H, Du D.-M. Org. Biomol. Chem. 2013; 11: 6215

Selected recent examples of aza-/oxa-/phospha-Michael addition:

10a Son EC, Kim SY, Kim S.-G. J. Org. Chem. 2021; 86: 6826
10b Sharma P, Gupta R, Bansal RK. Beilstein J. Org. Chem. 2021; 17: 2585
10c Tang Q.-G, Cai S.-L, Wang C.-C, Lin G.-Q, Sun X.-W. Org. Lett. 2020; 22: 3351
10d Tukhvatshin RS, Kucherenko AS, Nelyubina YV, Zlotin SG. Eur. J. Org. Chem. 2018; 7000
10e Zhu Y, Malerich JP, Rawal VH. Angew. Chem. Int. Ed. 2010; 49: 153

11a Marchetti LA, Kumawat LK, Mao N, Stephens JC, Elmes RB. P. Chem 2019; 5: 1398
11b Alemán J, Parra A, Jiang H, Jørgensen KA. Chem. Eur. J. 2011; 17: 6890
11c Davis AP, Draper SM, Dunne G, Ashton P. Chem. Commun. 1999; 2265

12a Rotger C, Soberats B, Quiñonero D, Frontera A, Ballester P, Benet-Bucholtz J, Deyà PM, Costa A. Eur. J. Org. Chem. 2008; 1864
12b Quiñonero D, Frontera A, Ballester P, Deyà PM. Tetrahedron Lett. 2000; 41: 2001

13 Okino T, Hoashi Y, Furukawa T, Xu X, Takemoto Y. J. Am. Chem. Soc. 2005; 127: 119
14 Schulz F, Sumerin V, Heikkinen S, Pedersen B, Wang C, Atsumi M, Leskelä M, Repo T, Pyykkö P, Petry W, Rieger B. J. Am. Chem. Soc. 2011; 133: 20245
15 Amendola V, Bergamaschi G, Boiocchi M, Fabbrizzi L, Milani M. Chem. Eur. J. 2010; 16: 4368
16 Quiñonero D, Frontera A, Suñer GA, Morey J, Costa A, Ballester P, Deyà PM. Chem. Phys. Lett. 2000; 326: 247
17 Ramalingam V, Domaradzki ME, Jang S, Muthyala RS. Org. Lett. 2008; 10: 3315

18a Usuda H, Kuramochi A, Kanai M, Shibasaki M. Org. Lett. 2004; 6: 4387
18b Davies HM. L, Jin Q. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 5472
18c Kanemasa S, Kanai T. J. Am. Chem. Soc. 2000; 122: 10710
18d Comprehensive Asymmetric Catalysis, Vols. I–III. Jacobsen EN, Pfaltz A, Yamamoto H. Springer; Berlin: 1999

19 Khatik GL, Kumar R, Chakraborti AK. Org. Lett. 2006; 8: 2433

20a Lađarević J, Božić B, Matović L, Nedelijković BB, Mijin D. Dyes Pigm. 2019; 162: 562
20b Feldblum ES, Arkin IT. Proc. Natl. Acad. Sci. U.S.A. 2014; 111: 4085
20c Rozas I, Alkorta I, Elguero J. J. Phys. Chem. A 1998; 102: 9925
20d Giguère PA. J. Raman Spectrosc. 1984; 15: 354

21 Chakraborti AK, Sharma L, Nayak MK. J. Org. Chem. 2002; 67: 2541

22a Chebolu R, Kommi DN, Kumar D, Bollineni N, Chakraborti AK. J. Org. Chem. 2012; 77: 10158
22b Zheng Y, Zhang J. ChemPhysChem 2010; 11: 65
22c Jung Y, Marcus RA. J. Am. Chem. Soc. 2007; 129: 5492

Selected examples:

23a Seth K, Raha Roy S, Pipaliya BV, Chakraborti AK. Chem. Commun. 2013; 49: 5886
23b Kumar D, Seth K, Kommi DN, Bhagat S, Chakraborti AK. RSC Adv. 2013; 3: 15157
23c Kommi DN, Kumar D, Seth K, Chakraborti AK. Org. Lett. 2013; 15: 1158
23d Kommi DN, Jadhavar PS, Kumar D, Chakraborti AK. Green Chem. 2013; 15: 798
23e Kommi DN, Kumar D, Chakraborti AK. Green Chem. 2013; 15: 756

24 Guo J, Wong MW. J. Org. Chem. 2017; 82: 4362

25a Popova EA, Pronina YA, Davtian AV, Nepochatyi GD, Petrov ML, Boitsov VM, Stepakov AV. Russ. J. Gen. Chem. 2022; 92: 287
25b Zhao B.-L, Li J.-H, Du D.-M. Chem. Rec. 2017; 17: 994
25c Chauhan P, Mahajan S, Kaya U, Hack D, Enders D. Adv. Synth. Catal. 2015; 357: 253

Selected examples:

26a Liu X.-Y, Qin Y. Green Synth. Catal. 2022; 3: 25
26b Taber DF, Tirunahari PK. Tetrahedron 2011; 67: 7195
26c Bandini M, Eichholzer A. Angew. Chem. Int. Ed. 2009; 48: 9608
26d Gupta L, Talwar A, Palne NS, Gupta S, Chauhan PM. S. Bioorg. Med. Chem. Lett. 2007; 17: 4075
26e Somei M, Yamada F. Nat. Prod. Rep. 2005; 22: 73
26f Skibo EB, Xing C, Dorr RT. J. Med. Chem. 2001; 44: 3545
26g Gribble GW. J. Chem. Soc., Perkin Trans. 1 2000; 1045
26h Sundberg RJ. Indoles . Meth-Cohn O. Academic Press; San Diego: 1996

27a Benetti S, Risi CD, Pollini GP, Zanirato V. Chem. Rev. 2012; 112: 2129
27b Gallienne E, Benazza M, Demailly G, Bolte J, Lemaire M. Tetrahedron 2005; 61: 4557
27c Qiao C, Ling K.-Q, Shepard EM, Dooley DM, Sayre LM. J. Am. Chem. Soc. 2006; 128: 6206
27d Wirsching J, Voss J, Adiwidjaja G, Balzarini J, Clercq ED. Bioorg. Med. Chem. Lett. 2001; 11: 1049
27e Clercq PJ. D. Chem. Rev. 1997; 97: 1755

28 Li Y.-H, Zhao B.-L, Gao Y, Du D.-M. Tetrahedron: Asymmetry 2014; 25: 1513

Selected examples:

29a Palmo C, Oiarbide M, Dias F, Ortiz A, Linden A. J. Am. Chem. Soc. 2001; 123: 5602
29b Apfel C, Banner DW, Bur D, Dietz M, Hirata T, Hubschwerlen C, Locher H, Page MG. P, Pirson W, Rossé G, Specklin J.-L. J. Med. Chem. 2000; 43: 2324
29c Procter DJ. J. Chem. Soc., Perkin Trans. 1 1999; 641
29d Groneberg RD, Burns CJ, Morrissette MM, Ullrich JW, Morris RL, Darnbrough S, Djuric SW, Condon SM, McGeehan GM, Labaudiniere R, Neuenschwander K, Scotese AC, Kline JA. J. Med. Chem. 1999; 42: 541
29e Beszant B, Bird J, Gaster LM, Harper GP, Hughes I, Karran EH, Markwell RE, Miles-Williams AJ, Smith SA. J. Med. Chem. 1993; 36: 4030

30 Liu Y, Sun B, Wang B, Wakem M, Deng L. J. Am. Chem. Soc. 2009; 131: 418
31 Dai L, Yang H, Chen F. Eur. J. Org. Chem. 2011; 5071
32 Paul A, Thomas R. ChemRxiv 2021; preprint
33 Annunziata R, Cinquini M, Cozzi F, Raimondi L. Tetrahedron Lett. 1988; 29: 2881
34 Zhao B.-L, Du D.-M. RSC Adv. 2014; 4: 27346
35 Laurence C, Mansour S, Vuluga D, Planchat A, Legros J. J. Org. Chem. 2021; 86: 4143

Selected examples:

36a Keller B, Cai Z, Muthike AK, Sahu PK, Kim H, Eshun A, Zimmerman PM, Zhang D, Goodson TIII. J. Phys. Chem. C 2018; 122: 27713
36b Romiszewski J, Puterová-Tokarová Z, Mieczkowski J, Gorecka E. New J. Chem. 2014; 38: 2927
36c O’Connor CJ, Roydhouse MD, Przybył AM, Wall MD, Southern JM. J. Org. Chem. 2010; 75: 2534
36d Li Y, Vamvounis G, Holdcroft S. Macromolecules 2002; 18: 6900

Selected examples:

37a Mondal B, Nandi S, Pan SC. Eur. J. Org. Chem. 2017; 4666
37b Brandau S, Maerten E, Jørgensen KA. J. Am. Chem. Soc. 2006; 128: 14986
37c Julienne K, Metzner P, Henryon V. J. Chem. Soc., Perkin Trans. 1 1999; 731
37d Hauptman E, Shapiro R, Marshall W. Organometallics 1998; 17: 4976
37e Julienne K, Metzner P. J. Org. Chem. 1998; 63: 4532

Selected examples:

38a Diana EJ, Kanchana US, Mathew TV. Org. Biomol. Chem. 2021; 19: 7995
38b Grigalunas M, Burhop A, Zinken S, Pahl A, Gally J.-M, Wild N, Mantel Y, Sievers S, Foley DJ, Scheel R, Strohmann C, Antonchick AP, Waldmann H. Nat. Commun. 2021; 12: 1883
38c Emami S, Ghanbarimasir Z. Eur. J. Med. Chem. 2015; 93: 539
38d Fridén-Saxin M, Seifert T, Landergren MR, Suuronen T, Lahtela-Kakkonen M, Jarho EM, Luthman K. J. Med. Chem. 2012; 55: 7104

39 Zhao B.-L, Liu L, Du D.-M. Eur. J. Org. Chem. 2014; 7850

Selected examples:

40a Inoue M, Sumii Y, Shibata N. ACS Omega 2020; 5: 10633
40b Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
40c Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
40d Shah P, Westwell AD. J. Enzyme Inhib. Med. Chem. 2007; 22: 527

Selected examples:

41a Zhu Y, Han J, Wang J, Shibata N, Sodeoka M, Soloshonok VA, Coelho JA. S, Toste FD. Chem. Rev. 2018; 118: 3887
41b Das P, Tokunaga E, Shibata N. Tetrahedron Lett. 2017; 58: 4803
41c Besset T, Jubault P, Pannecoucke X, Poisson T. Org. Chem. Front. 2016; 3: 1004
41d Huang Y.-Y, Yang X, Chen Z, Verpoort F, Shibata N. Chem. Eur. J. 2015; 21: 8664
41e Xu X.-H, Matsuzaki K, Shibata N. Chem. Rev. 2015; 115: 731
41f Savoie PR, Welch JT. Chem. Rev. 2015; 115: 1130

42a Kwiatkowski P, Dudziński K, Łyżwa D. Org. Lett. 2011; 13: 3624
42b Wen S, Li P, Wu H, Yu F, Liang X, Ye J. Chem. Commun. 2010; 46: 4806
42c Lu H.-H, Zhang F.-G, Meng X.-G, Duan S.-W, Xiao W.-J. Org. Lett. 2009; 11: 3946

Selected examples:

43a Pandey G, Mishra A, Khamrai J. Tetrahedron 2018; 74: 4903
43b Liu Y, Han S.-J, Liu W.-B, Stoltz BM. Acc. Chem. Res. 2015; 48: 740
43c Cozzi PG, Hilgraf R, Zimmermann N. Eur. J. Org. Chem. 2007; 5969
43d Bella M, Gasperi T. Synthesis 2009; 1583
43e Corey EJ, Guzman-Perez A. Angew. Chem. Int. Ed. 1998; 37: 388

44 Su Y, Ling J.-B, Zhang S, Xu P.-F. J. Org. Chem. 2013; 78: 11053
45 Ling J.-B, Su Y, Zhu H.-L, Wang G.-Y, Xu P.-F. Org. Lett. 2012; 14: 1090

46a Guin S, Saha HK, Patel AK, Gudimella SK, Biswas S, Samanta S. Tetrahedron 2020; 76: 131338
46b Chauhan P, Kaya U, Enders D. Adv. Synth. Catal. 2017; 359: 888
46c Meng F, Li X, Torker S, Shi Y, Shen X, Hoveyda AH. Nature 2016; 537: 387
46d Pei Q.-L, Sun H.-W, Wu Z.-J, Du X.-L, Zhang X.-M, Yuan W.-C. J. Org. Chem. 2011; 76: 7849
46e Krause N. J. Org. Chem. 1992; 57: 3509

47 Scott KA, Njardarson JT. Top. Curr. Chem. 2018; 376: 5

48a Gürdere MB, Gezegen H, Budak Y, Ceylan M. Phosphorus, Sulfur Silicon Relat. Elem. 2012; 87: 889
48b Hui Y, Jiang J, Wang W, Chen W, Cai Y, Lin L, Liu X, Feng X. Angew. Chem. Int. Ed. 2010; 49: 4290
48c Dai L, Wang S.-X, Chen F.-E. Adv. Synth. Catal. 2010; 352: 2137

49 Hasılcıoğulları D, Tanyeli C. Tetrahedron Lett. 2018; 59: 1414

The H-bonding in water model:

50a Bakó I, Pusztai L, Temleitner L. Sci. Rep. 2017; 1073
50b Takamuku T, Saisho K, Nozawa S, Yamaguchi T. J. Mol. Liq. 2005; 119: 133
50c Khan A. J. Phys. Chem. B 2000; 104: 11268

Selected examples:

51a Duan J, Cheng Y, Li R, Li P. Org. Chem. Front. 2016; 3: 1614
51b Pizzirani D, Roberti M, Grimaudo S, Cristina AD, Pipitone RM, Tolomeo M, Recanatini M. J. Med. Chem. 2009; 52: 6936
51c Nicolaou KC, Montagnon T, Vassilikogiannakis G, Mathison CJ. N. J. Am. Chem. Soc. 2005; 127: 8872

52 Mahajan S, Chauhan P, Blümel M, Puttreddy R, Rissanen K, Raabe G, Enders D. Synthesis 2016; 48: 1131

Selected examples:

53a Alves NG, Alves AJ. S, Soares MI. L, Pinho e Melo TM. V. D. Adv. Synth. Catal. 2021; 363: 2464
53b Alves NG, Bártolo I, Alves AJ. S, Frontina D, Francisco D, Lopes SM. M, Soares MI. L, Simões CJ. V, Prudêncio M, Taveira N, Pinho e Melo TM. V. D. Eur. J. Med. Chem. 2021; 219: 113439
53c Alves AJ. S, Alves NG, Caratão CC, Esteves MI. M, Frontina D, Bártolo I, Soares MI. L, Prudêncio M, Taveira N, Pinho e Melo TM. V. D. Curr. Top. Med. Chem. 2020; 20: 140
53d Benfatti F, Cardillo G, Gentilucci L, Tolomelli A. Bioorg. Med. Chem. Lett. 2007; 17: 1946

Selected recent examples:

54a Nájera C, Foubelo F, Sansano JM, Yus M. Tetrahedron 2022; 106-107: 132629
54b Manna MS, Mukherjee S. Org. Biomol. Chem. 2015; 13: 18
54c Kalstabakken KA, Harned AM. Tetrahedron 2014; 70: 957
54d Maertens G, Ménard M.-A, Canesi S. Synthesis 2014; 46: 1573

Selected recent examples:

55a Costanzo M, Cortigiani M, Gillick-Healy MW, Kelly BG, Monasterolo C, Adamo MF. A. Eur. J. Org. Chem. 2021; 4560
55b Li F, Wang J, Xu M, Zhao X, Zhou X, Zhao W.-X, Liu L. Org. Biomol. Chem. 2016; 14: 3981
55c Li Y, Yang S, Wen G, Lin Q, Zhang G, Qiu L, Zhang X, Du G, Fang X. J. Org. Chem. 2016; 81: 2763
55d Rubush DM, Rovis T. Synlett 2014; 713
55e Wu W, Li X, Huang H, Yuan X, Lu J, Zhu K, Ye J. Angew. Chem. Int. Ed. 2013; 52: 1743
55f Takizawa S, Nguyen TM.-N, Grossmann A, Suzuki M, Enders D, Sasai H. Tetrahedron 2013; 69: 1202

Selected recent examples:

56a Zhang R, Guo W, Duan M, Houk KN, Sun J. Angew. Chem. Int. Ed. 2019; 58: 18055
56b Naganawa Y, Kawagishi M, Ito J.-i, Nishiyama H. Angew. Chem. Int. Ed. 2016; 55: 6873
56c Takagi R, Nishi T. Org. Biomol. Chem. 2015; 13: 11039
56d Wang Z, Sheong FK, Sung HH. Y, Williams ID, Lin Z, Sun J. J. Am. Chem. Soc. 2015; 137: 5895
56e Miyamae N, Watanabe N, Moritaka M, Nakano K, Ichikawa Y, Kotsuki H. Org. Biomol. Chem. 2014; 12: 5847

57 Chauhan P, Mahajan S, Kaya U, Valkonen A, Rissanen K, Enders D. Adv. Synth. Catal. 2016; 358: 3173

Selected examples:

58a Chouchène N, Toumi A, Boudriga S, Edziri H, Sobeh M, Abdelfattah MA. O, Askri M, Knorr M, Strohmann C, Brieger L, Soldera A. Molecules 2022; 27: 582
58b Vargas E, Echeverri F, Vélez ID, Robledo SM, Quiñones W. Molecules 2017; 22: 2041
58c Bolognesi ML, Bartolini M, Cavalli A, Andrisano V, Rosini M, Minarini A, Melchiorre C. J. Med. Chem. 2004; 47: 5945
58d van Vliet LA, Rodenhuis N, Dijkstra D, Wikström H, Pugsley TA, Serpa KA, Meltzer LT, Heffner TG, Wise LD, Lajiness ME, Huff RM, Svensson K, Sundell S, Lundmark M. J. Med. Chem. 2000; 43: 2871

59a Eftekhari-Sis B, Zirak M. Chem. Rev. 2015; 115: 151
59b Desimoni G, Faita G, Quadrelli P. Chem. Rev. 2013; 113: 5924

Selected recent examples:

60a Guan X.-K, Liu G.-F, An D, Zhang H, Zhang S.-Q. Org. Lett. 2019; 21: 5438
60b Xu J, Hu L, Hu H, Ge S, Liu X, Feng X. Org. Lett. 2019; 21: 1632
60c Huang K.-X, Xie M.-S, Zhang Q.-Y, Niu H.-Y, Qu G.-R, Guo H.-M. Org. Lett. 2018; 20: 5398
60d Xie L, Yu X, Li J, Zhang Z, Qin Z, Fu B. Eur. J. Org. Chem. 2017; 657
60e Zhong X, Lv J, Luo S. Org. Lett. 2017; 19: 3331
60f Zhang M.-L, Wu Z.-J, Zhao J.-Q, Luo Y, Xu X.-Y, Zhang X.-M, Yuan W.-C. Org. Lett. 2016; 18: 5110
60g Huang H, Konda S, Zhao JC.-G. Angew. Chem. Int. Ed. 2016; 55: 2213

61 Mo Y, Zhang X, Yao Y, Duan C, Ye L, Shi Z, Zhao Z, Li X. J. Org. Chem. 2021; 86: 4448
62 Yang Y, Du D. Chin. J. Chem. 2014; 32: 853

Selected examples:

63a Dong X.-Q, Fang X, Tao H.-Y, Zhou X, Wang C.-J. Adv. Synth. Catal. 2012; 354: 1141
63b Rana NK, Singh VK. Org. Lett. 2011; 13: 6520
63c Ricci P, Carlone A, Bartoli G, Bosco M, Sambri L, Melchiorre P. Adv. Synth. Catal. 2008; 350: 49
63d Suresh P, Pitchumani K. Tetrahedron: Asymmetry 2008; 19: 2037
63e Zu L, Wang J, Li H, Xie H, Jiang W, Wang W. J. Am. Chem. Soc. 2007; 129: 1036

64 Zhao B.-L, Du D.-M. Org. Biomol. Chem. 2014; 12: 1585

Selected examples:

65a Nie J, Guo H.-C, Cahard D, Ma J.-A. Chem. Rev. 2010; 111: 455
65b Smits R, Cadicamo CD, Burger K, Koksch B. Chem. Soc. Rev. 2008; 37: 1727

66a Wang J, Sánchez-Roselló M, Aceña JL, del Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H. Chem. Rev. 2014; 114: 2432
66b O’Hagan D. J. Fluorine Chem. 2010; 131: 1071

67 Hu W.-F, Zhao J.-Q, Chen X.-Z, Zhou M.-Q, Zhang X.-M, Xu X.-Y, Yuan W.-C. Tetrahedron 2019; 75: 2206

68a Zhang H, Du X, Tang Y, Lu X, Zhou L, Zheng C, Lin H, Tao S. Front. Chem. 2020;
68b Esterhuysen C, Heßelmann A, Clark T. ChemPhysChem 2017; 18: 772
68c Chen J, Meng S, Wang L, Tang H, Huang Y. Chem. Sci. 2015; 6: 4184
68d Dalvit C, Invernizzi C, Vulpetti A. Chem. Eur. J. 2014; 20: 11058

Selected examples:

69a Lesuisse D, Deprez P, Albert E, Duc TT, Sortais B, Gofflo D, Jean-Baptiste V, Marquette J.-P, Schoot B, Sarubbi E, Lange G, Broto P, Mandine E. Bioorg. Med. Chem. Lett. 2001; 11: 2127
69b Arakawa M, Sasaki M, Ohmori M, Harada K, Fujimura A. Eur. J. Clin. Pharmacol. 2001; 56: 775
69c Amblard M, Daffix I, Bedos P, Bergé G, Pruneau D, Paquet J.-L, Luccarini J.-M, Bélichard P, Dodey P, Martinez J. J. Med. Chem. 1999; 42: 4185
69d Corelli F, Manetti F, Tafi A, Campiani G, Nacci V, Botta M. J. Med. Chem. 1997; 40: 125

70a Kaur R, Singh K, Singh R. Chem. Biol. Lett. 2016; 3: 18
70b Yanagisawa H, Ishihara S, Ando A, Kanazaki T, Miyamoto S, Koike H, Iijima Y, Oizumi K, Matsushita Y, Hata T. J. Med. Chem. 1987; 30: 1984

71 Gharui C, Prakash S, Chopra D, Pan SC. Org. Biomol. Chem. 2020; 18: 2828
72 Burtoloso AC. B, Dias RM. P, Bernardim B. Acc. Chem. Res. 2015; 48: 921
73 Santiago JV, Burtoloso AC. B. Eur. J. Org. Chem. 2018; 2822
74 Momo PB, Mizobüchi EF, Echemendía R, Baddeley I, Grayson MN, Burtoloso AC. B. J. Org. Chem. 2022; 87: 3482

Selected examples:

75a Ielo L, Pace V, Holzer W, Rahman MM, Meng G, Szostak R, Szostak M. Chem. Eur. J. 2020; 26: 16246
75b Kaiser D, Bauer A, Lemmerer M, Maulide N. Chem. Soc. Rev. 2018; 47: 7899
75c Allgäuer DS, Jangra H, Asahara H, Li Z, Chen Q, Zipse H, Ofial AR, Mayr H. J. Am. Chem. Soc. 2017; 139: 13318
75d Dey A, Sasmal S, Seth K, Lahiri GK, Maiti D. ACS Catal. 2017; 7: 433
75e Weires NA, Baker EL, Garg NK. Nat. Chem. 2016; 8: 75
75f Baker EL, Yamano MM, Zhou Y, Anthony SM, Garg NK. Nat. Commun. 2016; 7: 11554
75g Ruider SA, Maulide N. Angew. Chem. Int. Ed. 2015; 54: 13856
75h Hie L, Nathel NF. F, Shah TK, Baker EL, Hong X, Yang Y.-F, Liu P, Houk KN, Garg NK. Nature 2015; 524: 79

76a Bennet AJ, Wang QP, Slebocka-Tilk H, Somayaji V, Brown RS. J. Am. Chem. Soc. 1990; 112: 6383
76b Slebocka-Tilk H, Brown RS. J. Org. Chem. 1987; 52: 805
76c Pauling L, Corey RB, Branson HR. Proc. Natl. Acad. Sci. U.S.A. 1951; 37: 205

77 Formica M, Rozsar D, Su G, Farley AJ. M, Dixon DJ. Acc. Chem. Res. 2020; 53: 2235

Selected examples:

78a Su G, Thomson CJ, Yamazaki K, Rozsar D, Christensen KE, Hamlin TA, Dixon DJ. Chem. Sci. 2021; 12: 6064
78b Golec JC, Carter EM, Ward JW, Whittingham WG, Simón L, Paton RS, Dixon DJ. Angew. Chem. Int. Ed. 2020; 59: 17417
78c Thomson CJ, Barber DM, Dixon DJ. Angew. Chem. Int. Ed. 2020; 59: 5359
78d Formica M, Sorin G, Farley AJ. M, Díaz J, Paton RS, Dixon DJ. Chem. Sci. 2018; 9: 6969
78e Fulton JL, Horwitz MA, Bruske EL, Johnson JS. J. Org. Chem. 2018; 83: 3385
78f Farley AJ. M, Sandford C, Dixon DJ. J. Am. Chem. Soc. 2015; 137: 15992

79 Rozsar D, Formica M, Yamazaki K, Hamlin TA, Dixon DJ. J. Am. Chem. Soc. 2022; 144: 1006

80a Chen M, Li Z, Shao X, Maienfisch P. J. Agric. Food Chem. 2022; 70: 11123
80b Gray KC, Heider P, McGough P, Ondari M, Devaraj J, Yang Q, Frycek G, Graham B, Neuman J, Lorsbach BA, Zhang Y. Org. Process Res. Dev. 2019; 23: 2142
80c Yang Q, Li X, Lorsbach BA, Muhuhi JM, Roth JA, Gray K, Podhorez DE. Org. Process Res. Dev. 2019; 23: 2133
80d Yang Q, Li X, Lorsbach BA, Roth GA, Podhorez DE, Ross RJr, Niyaz N, Buysse A, Knueppel D, Nissen J. Org. Process Res. Dev. 2019; 23: 2122

81 Hamza A, Schubert G, Soós T, Pápai I. J. Am. Chem. Soc. 2006; 128: 13151

82a Siwach A, Verma PK. BMC Chem. 2021; 15: 12
82b Gopalakrishnan AK, Angamaly SA, Velayudhan MP. ChemistrySelect 2021; 6: 10918
82c Chopra PN, Sahu JK. Curr. Drug Discovery Technol. 2020; 17: 574
82d Weinreb SM. Nat. Prod. Rep. 2007; 24: 931

Selected examples:

83a İbişoğlu H, Atilla D, Tümay SO, Şenocak A, Duygulu E, Yuksel F. J. Mol. Struct. 2020; 1208: 127888
83b Chen S.-C. CrystEngComm 2016; 18: 6543
83c Khan MN, Pal S, Karamthulla S, Choudhury LH. RSC Adv. 2014; 4: 3732
83d Zhang Z, Xie F, Jia J, Zhang W. J. Am. Chem. Soc. 2010; 132: 15939
83e Miller SJ. Acc. Chem. Res. 2004; 37: 601
83f Crudden CM, Allen DP. Coord. Chem. Rev. 2004; 248: 2247
83g Dupont J, de Souza RF, Suarez PA. Z. Chem. Rev. 2002; 102: 3667

84a Yang J, Farley AJ. M, Dixon DJ. Chem. Sci. 2017; 8: 606
84b White JD, Shaw S. Chem. Sci. 2014; 5: 2200
84c Fang X, Li J, Wang C.-J. Org. Lett. 2013; 15: 3448
84d Uraguchi D, Kinoshita N, Nakashima D, Ooi T. Chem. Sci. 2012; 3: 3161

85 Jha RK, Rout S, Joshi H, Das A, Singh VK. Tetrahedron 2019; 76: 130800

Selected examples:

86a Lopes AA, Chioca B, Musquiari B, Crevelin EJ, França S. dC, da Silva MF. d. G. F, Pereira AM. S. Sci. Rep. 2019; 9: 11349
86b Trost BM, Bringley DA, Zhang T, Cramer N. J. Am. Chem. Soc. 2013; 135: 16720
86c Wanner MJ, Ingemann S, van Maarseveen JH, Hiemstra H. Eur. J. Org. Chem. 2013; 1100
86d Day J, Uroos M, Castledine RA, Lewis W, McKeever-Abbas B, Dowden J. Org. Biomol. Chem. 2013; 11: 6502
86e Zhou F, Liu Y.-L, Zhou J. Adv. Synth. Catal. 2010; 352: 1381
86f Lin H, Danishefsky SJ. Angew. Chem. Int. Ed. 2003; 42: 36

87 Duan S.-W, Li Y, Liu Y.-Y, Zou Y.-Q, Shi D.-Q, Xiao W.-J. Chem. Commun. 2012; 48: 5160

Selected examples:

88a Seifert T, Malo M, Kokkola T, Engen K, Fridén-Saxin M, Walén EA. A, Lahtela-Kakkonen M, Jarho E.-M, Luthman K. J. Med. Chem. 2014; 57: 9870
88b Conti C, Monaco LP, Desideri N. Bioorg. Med. Chem. 2011; 19: 7357
88c Shi Y.-L, Shi M. Org. Biomol. Chem. 2007; 5: 1499
88d Afantitis A, Melagraki G, Sarimveis H, Koutentis PA, Markopoulos J, Igglessi-Markopoulou O. Bioorg. Med. Chem. 2006; 14: 6686
88e Kang JG, Shin SY, Kim MJ, Bajpai V, Maheshwari DK, Kang SC. J. Antibiot. 2004; 57: 726

89 Yang W, Yang Y, Du D.-M. Org. Lett. 2013; 15: 1190

90a Bi X, Pasunooti KK, Tareq AH, Takyi-Williams J, Liu C.-F. Org. Biomol. Chem. 2016; 14: 5282
90b Cheng Y, Peng H, Chen W, Ni N, Ke B, Dai C, Wang B. Chem. Eur. J. 2013; 19: 4036
90c Nguyen DP, Elliott T, Holt M, Muir TW, Chin JW. J. Am. Chem. Soc. 2011; 133: 11418

91 Yang W, Du D.-M. Org. Biomol. Chem. 2012; 10: 6876