Multiselective Catalytic Asymmetric Reactions Using α-Keto Esters as Pronucleophiles

Yoshihiro Sohtome; Mikiko Sodeoka

doi:10.1055/s-0039-1690722

Synlett, Inhaltsverzeichnis

Synlett 2020; 31(06): 523-534
DOI: 10.1055/s-0039-1690722

account

Multiselective Catalytic Asymmetric Reactions Using α-Keto Esters as Pronucleophiles

Yoshihiro Sohtome ∗

^aRIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan

^bRIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan eMail: sohtome@riken.jp eMail: sodeoka@riken.jp

,

Mikiko Sodeoka ∗

^aRIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan

^bRIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan eMail: sohtome@riken.jp eMail: sodeoka@riken.jp

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

In memory of Professor Dieter Enders

Published as part of the ISySyCat2019 Special Issue

Abstract

In the reactions of simple starting materials, precise catalytic control of the stereochemical outcome (enantio- and diastereoselectivity), as well as chemoselectivity and regioselectivity is an efficient approach to increase molecular complexity with minimal use of protecting groups. Here, we introduce our ongoing studies on asymmetric catalytic reactions using α-keto esters as pronucleophiles or formal 1,3-dipolarophiles. Capitalizing on the high tunability of our late transition-metal complexes with a suitable basic counteranion, we have established a range of multiselective catalytic protocols starting from α-keto esters to provide a wide variety of stereochemically complex molecules incorporating adjacent stereocenters.

1 Introduction

2 Catalytic Asymmetric Monofluorination with NSFI

3 Catalytic Asymmetric Michael Reaction with Nitroolefins

4 Catalytic Asymmetric [3+2] Cycloaddition with (E)-Nitrones

5 Catalytic Asymmetric [3+2] Cycloaddition with Nitrile Oxides

6 Summary

Key words

α-keto esters - enolates - chemoselectivity - stereoselectivity - regioselectivity - transition metals - asymmetric catalysis - nucleophilic addition

Volltext

Referenzen

References and Notes
1 For a review on selectivity, see: Trost BM. Science 1983; 219: 245
2 For a review on selective catalysis, see: Mahatthananchai J, Dumas AM, Bode JW. Angew. Chem. Int. Ed. 2012; 51: 10954

For reviews on protecting-group-free synthesis, see:

3a Hoffman RW. Synthesis 2006; 3531
3b Young IS, Baran PS. Nat. Chem. 2009; 1: 193

4 For a review on atom economy, see: Trost BM. Science 1991; 254: 1471
5 For a review on step economy, see: Wender PA, Verma VA, Paxton TJ, Pillow TH. Acc. Chem. Res. 2008; 41: 40
6 For a review on redox economy, see: Burns NZ, Baran PS, Hoffman RW. Angew. Chem. Int. Ed. 2009; 48: 2854
7 For a review on pot economy, see: Hayashi Y. Chem. Sci. 2016; 7: 866

For reviews on chemoselectivity, see:

8a Shenvi RA, O’Malley DP, Baran PS. Acc. Chem. Res. 2009; 42: 530
8b Afagh NA, Yudin AK. Angew. Chem. Int. Ed. 2010; 49: 262

For our work on catalytic asymmetric Michael reactions of 1,3-dicarbonyl compounds, see:

9a Hamashima Y, Hotta D, Sodeoka M. J. Am. Chem. Soc. 2002; 124: 11240
9b Hamashima Y, Hotta D, Umebayashi N, Tsuchiya Y, Suzuki T, Sodeoka M. Adv. Synth. Catal. 2005; 347: 1576
9c Hayamizu K, Terayama N, Hashizume D, Dodo K, Sodeoka M. Tetrahedron 2015; 71: 6594

For our accounts, see:

10a Sodeoka M, Hamashima Y. Chem. Commun. 2009; 5787
10b Sodeoka M, Hamashima Y. Pure Appl. Chem. 2008; 80: 763
10c Sodeoka M, Hamashima Y. Pure Appl. Chem. 2006; 78: 477
10d Hamashima Y, Sodeoka M. Synlett 2006; 1467
10e Sodeoka M, Hamashima Y. Bull. Chem. Soc. Jpn. 2005; 78: 941
10f Hamashima Y, Sodeoka M. Chem. Rec. 2004; 4: 231

11 Braun M. Modern Enolate Chemistry . Wiley-VCH; Weinheim: 2016

For our work on catalytic asymmetric halogenations of 1,3-dicarbonyl compounds, see:

12a Hamashima Y, Yagi K, Takano H, Tamás L, Sodeoka M. J. Am. Chem. Soc. 2002; 124: 14530
12b Hamashima Y, Takano H, Hotta D, Sodeoka M. Org. Lett. 2003; 5: 3225
12c Hamashima Y, Suzuki T, Takano H, Shimura H, Tsuchiya Y, Moriya K, Goto T, Sodeoka M. Tetrahedron 2006; 62: 7168
12d Suzuki T, Goto T, Hamashima Y, Sodeoka M. J. Org. Chem. 2007; 72: 246

For our work on catalytic asymmetric Mannich-type reactions of 1,3-dicarbonyl compounds, see:

13a Hamashima Y, Sasamoto N, Hotta D, Somei H, Umebayashi N, Sodeoka M. Angew. Chem. Int. Ed. 2005; 44: 1525
13b Sasamoto N, Dubs C, Hamashima Y, Sodeoka M. J. Am. Chem. Soc. 2006; 128: 14010
13c Dubs C, Hamashima Y, Sasamoto N, Seidel TM, Suzuki S, Hashizume D, Sodeoka M. J. Org. Chem. 2008; 73: 5859
13d Hamashima Y, Sasamoto N, Umebayashi N, Sodeoka M. Chem. Asian J. 2008; 3: 1443

For our work on catalytic asymmetric aldol-type reactions of 1,3-dicarbonyl compounds, see:

14a Fukuchi I, Hamashima Y, Sodeoka M. Adv. Synth. Catal. 2007; 349: 509
14b Umebayashi N, Hamashima Y, Hashizume D, Sodeoka M. Angew. Chem. Int. Ed. 2008; 47: 4196

15a Nakamura A, Lectard S, Hashizume D, Hamashima Y, Sodeoka M. J. Am. Chem. Soc. 2010; 132: 4036
15b Nakamura A, Lectard S, Shimizu R, Hamashima Y, Sodeoka M. Tetrahedron: Asymmetry 2010; 21: 1682

16 Suzuki S, Kitamura Y, Lectard S, Hamashima Y, Sodeoka M. Angew. Chem. Int. Ed. 2012; 51: 4581
17 Sohtome Y, Nakamura G, Muranaka A, Hashizume D, Lectard S, Tsuchimoto T, Uchiyama M, Sodeoka M. Nat. Commun. 2017; 8: 14875
18 Bartlett SL, Sohtome Y, Hashizume D, White PS, Sawamura M, Johnson JS, Sodeoka M. J. Am. Chem. Soc. 2017; 139: 8661

For reviews on the use of α-keto esters as pronucleophiles, see:

19a Raimondi W, Bonne D, Rodriguez J. Chem. Commun. 2012; 48: 6763
19b Raimondi W, Bonne D, Rodriguez J. Angew. Chem. Int. Ed. 2012; 51: 40

For leading work on α-keto esters as pronucleophiles in catalytic asymmetric homo-aldol reaction, see:

20a Juhl K, Gathergood N, Jørgensen KA. Chem. Commun. 2000; 2211
20b Dambruoso P, Massi A, Dondoni A. Org. Lett. 2005; 7: 4657

In Mannich-type reaction with α-imino esters:

20c Juhl K, Gathergood N, Jørgensen KA. Angew. Chem. Int. Ed. 2001; 40: 2995

In catalytic asymmetric amination reaction with azodicarboxylates:

20d Juhl K, Jørgensen KA. J. Am. Chem. Soc. 2002; 124: 2420

In catalytic asymmetric cross-aldol reaction:

20e Torii H, Nakadai M, Ishihara K, Saito S, Yamamoto H. Angew. Chem. Int. Ed. 2004; 43: 1983
20f Gathergood N, Juhl K, Poulse TB, Thordrup K, Jørgensen KA. Org. Biomol. Chem. 2004; 2: 1077
20g Vincent J.-M, Margottin C, Berlande M, Cavagnat D, Buffeteau T, Landais Y. Chem. Commun. 2007; 4782

For leading work on α-keto amides as pronucleophiles for catalytic asymmetric Mannich-type reactions with N-thiophenesulfonyl imines, see:

21a Lu G, Morimoto H, Matsunaga S, Shibasaki M. Angew. Chem. Int. Ed. 2008; 47: 6847

For other recent examples, see:

21b Muthukumar A, Sangeetha S, Sekar G. Org. Biomol. Chem. 2018; 16: 7068 ; other references cited therein

22 Kanehisa M, Sato Y, Furumichi M, Morishima K, Tanabe M. Nucleic Acids Res. 2019; 47: D590

For selected reviews, see:

23a Shibasaki M, Kanai M. Chem. Rev. 2008; 108: 2853
23b Liu Y.-L, Lin X.-T. Adv. Synth. Catal. 2019; 361: 876

24 For a recent review, see: Bartlett SL, Johnson JS. Acc. Chem. Res. 2017; 50: 2284
25 Hashimoto K, Shirahama H. Tetrahedron Lett. 1991; 32: 2625

For general reviews on catalytic asymmetric fluorinations, see:

26a Lectard S, Hamashima Y, Sodeoka M. Adv. Synth. Catal. 2010; 352: 2708
26b Yang X, Wu T, Phipps RJ, Toste FD. Chem. Rev. 2015; 115: 826
26c Zhu Y, Han J, Wang J, Shibata N, Sodeoka M, Soloshonok VA. Coelho J. A. S, Toste FD. Chem. Rev. 2018; 118: 3887

27 With phosphonate esters, see: Hamashima Y, Suzuki T, Shimura Y, Shimizu T, Umebayashi N, Tamura T, Sasamoto N, Sodeoka M. Tetrahedron Lett. 2005; 46: 1447
28 With oxindoles: Hamashima Y, Suzuki T, Takano H, Shimura Y, Sodeoka M. J. Am. Chem. Soc. 2005; 127: 10164
29 With α-aryl-α-cyanophosphate esters: Moriya K, Hamashima Y, Sodeoka M. Synlett 2007; 1139
30 With N-acyl thiazolinethiones: Suzuki T, Hamashima Y, Sodeoka M. Angew. Chem. Int. Ed. 2007; 46: 5435

For the synthesis of (±)-β-fluoro-α-keto esters, see:

31a Ourari A, Condom R, Guedi R. Can. J. Chem. 1982; 60: 2707
31b Okonya JF, Johnson MC, Hoffman RV. J. Org. Chem. 1998; 63: 6409

32 For a recent review on metal-catalyzed asymmetric Michael reaction, see: Zheng, K.; Liu, X.; Feng, X. Chem. Rev. 2018, 118, 7586; and other references cited therein.
33 For a recent review on nickel(II)-catalyzed asymmetric conjugate additions, see: Pellissier H. Adv. Synth. Catal. 2015; 357: 2745

For reviews that involve metal-dependent enantioswitching, see:

34a Beletskyaya IP, Nájera C, Yus M. Chem. Rev. 2018; 118: 5080
34b Escorihuela J, Burguete MI, Luis SV. Chem. Soc. Rev. 2013; 42: 5595

35a Evans DA, Seidel D. J. Am. Chem. Soc. 2005; 127: 9958
35b Evans DA, Mito S, Seidel D. J. Am. Chem. Soc 2007; 129: 11583

For catalytic Michael/Michael/Henry reactions starting from α-keto esters, see:

36a Shi D, Xie Y, Zhou H, Xia C, Huang HM. Angew. Chem. Int. Ed. 2012; 51: 1248
36b Chen Y, Liu X, Luo W, Feng X. Synlett 2017; 28: 966

37 For catalytic Michael–Michael–Henry reactions starting from α-keto amides, see: Baslé O, Raimondi W, Duque M. delM. S, Bonne D, Constantieux T, Rodriguez J. Org. Lett. 2010; 12: 5246

38a Grondal C, Jeanty M, Enders D. Nat. Chem. 2010; 2: 167
38b Albrecht L, Jiang H, Jørgensen KA. Angew. Chem. Int. Ed. 2011; 50: 8492
38c Pellissier H. Adv. Synth. Catal. 2012; 354: 237
38d Volla CM. R, Atodiresei I, Rueping M. Chem. Rev. 2014; 114: 2390

39a Sasaki S, Suzuki H, Ouchi H, Asakawa T, Inai M, Sakai R, Shimamoto K, Hamashima Y, Kan T. Org. Lett. 2014; 16: 564
39b Ouchi H, Asahina A, Asakawa T, Inai M, Hamashima Y, Kan T. Org. Lett. 2014; 16: 1980
39c Inai M, Ouchi H, Asahina A, Asakawa T, Hamashima Y, Kan T. Chem. Pharm. Bull. 2016; 64: 723

40 For a general review on catalytic asymmetric [3+2] cycloadditions, see: Hashimoto T, Maruoka K. Chem. Rev. 2015; 115: 5366
41 For a recent review on biologically active isoxazolidines, see: Berthet M, Cheviet T, Dujardin G, Parrot I, Martinez J. Chem. Rev. 2016; 116: 15235

For selected examples of catalytic asymmetric IED [3+2] cycloadditions of nitrones, see:

42a Seerden J.-PG, Scholte op Reimer AW. A, Scheeren HW. Tetrahedron Lett. 1994; 35: 4419
42b Seerden J.-PG, Kuypers MM. M, Scheeren HW. Tetrahedron: Asymmetry 1995; 6: 1441
42c Seerden J.-PG. Boeren M. M. M, Scheeren HW. Tetrahedron 1997; 53: 11843
42d Simonsen KB, Bayón P, Hazell RG, Gothelf KV, Jørgensen KA. J. Am. Chem. Soc. 1999; 121: 3845
42e Jensen KB, Hazell RG, Jørgensen KA. J. Org. Chem. 1999; 64: 2353
42f Jensen KB, Roberson M, Jørgensen KA. J. Org. Chem. 2000; 65: 9080
42g Ashizawa T, Ohtsuki N, Miura T, Ohya M, Shinozaki T, Ikeno T, Yamada T. Heterocycles 2006; 68: 1801
42h Jiao P, Nakashima D, Yamamoto H. Angew. Chem. Int. Ed. 2008; 47: 2411
42i Yanagisawa A, Izumiseki A, Sugita T, Kushihara N, Yoshida K. Synlett 2012; 107

43 Inouye Y, Hara J, Kakisawa H. Chem. Lett. 1980; 9: 1407

For selected reviews, see:

44a Dugave C, Demange L. Chem. Rev. 2003; 103: 2475
44b Vlatkovic M, Collins BS. L, Feringa BL. Chem. Eur. J. 2016; 22: 17080

45 Fischer E. Ber. Dtsch. Chem. Ges. 1894; 27: 3189

For reviews, see:

46a Crawford JM, Sigman MS. Synthesis 2019; 51: 1021
46b Romanazzi G, Degennaro L, Mastrorilli P, Luisi R. ACS Catal. 2017; 7: 4100
46c Sohtome Y, Nagasawa K. Chem. Commun. 2012; 48: 7777

For reviews on chirality at metal, see:

47a Meggers E. Eur. J. Inorg. Chem. 2011; 2911
47b Gong L, Chen L.-A, Meggers E. Angew. Chem. Int. Ed. 2014; 53: 10868
47c Constable EC. Chem. Soc. Rev. 2013; 42: 1637
47d Ehnbom A, Ghosh SK, Lewis KG, Gladysz JA. Chem. Soc. Rev. 2016; 45: 6799
47e Zhang L, Meggers E. Acc. Chem. Res. 2017; 50: 320
47f Huang X, Meggers E. Acc. Chem. Res. 2019; 52: 833

For reviews on achiral additive effect in asymmetric catalysis, see:

48a Vogl EM, Gröger H, Shibasaki M. Angew. Chem. Int. Ed. 1999; 38: 1570
48b Hong L, Sun W, Yang D, Li G, Wang R. Chem. Rev. 2016; 116: 4006

For reviews on catalytic asymmetric [3+2] cycloadditions of nitrile oxides, see:

49a Roscales S, Plumet J. Org. Biomol. Chem. 2018; 16: 8446
49b Rane D, Sibi M. Curr. Org. Synth. 2011; 8: 616

For recent examples of catalytic IED asymmetric [3+2] cycloadditions of nitrile oxides, see:

50a Suga H, Hashimoto Y, Toda Y, Fukushima K, Esaki H, Kikuchi A. Angew. Chem. Int. Ed. 2017; 56: 11936
50b Toda Y, Koyama M, Esaki H, Fukushima K, Suga H. Heterocycles 2018; 97: 147

51 Yu Z.-X, Caramella P, Houk KN. J. Am. Chem. Soc. 2003; 125: 15420
52 Huisgen R, Wilhelm M. Tetrahedron Lett. 1961; 2: 583
53 The precise geometry could not be determined.
54 Metal-dependent enantioswitching was also observed. (R,R)-20 was obtained as the major product with Ni(II)–(R,R)-diamine complex. In contrast, the (S,S)-20 required the Cu(II)–(R,R)-diamine complex.
55 Zhu MK, Zhao JF, Loh TP. J. Am. Chem. Soc. 2010; 132: 6284