Palladium-Catalyzed Asymmetric Allylic Alkylation of Azlactones: An Efficient Access to Unsaturated Trifluoromethylated α-Amino Acid Derivatives Possessing α-Quaternary Stereogenic Centers

Shuaibo Zhang; Luyang Sun; Dong Li; Jinfeng Zhao; Jingping Qu; Yuhan Zhou

doi:10.1055/a-2360-8289

Synthesis, Table of Contents

Synthesis 2024; 56(20): 3220-3232
DOI: 10.1055/a-2360-8289

paper

Palladium-Catalyzed Asymmetric Allylic Alkylation of Azlactones: An Efficient Access to Unsaturated Trifluoromethylated α-Amino Acid Derivatives Possessing α-Quaternary Stereogenic Centers

Shuaibo Zhang

^aState Key Laboratory of Fine Chemicals, Department of Pharmaceutical Sciences, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, P. R. of China

,

Luyang Sun

^bState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, P. R. of China

,

Dong Li

^aState Key Laboratory of Fine Chemicals, Department of Pharmaceutical Sciences, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, P. R. of China

,

Jinfeng Zhao

^cInstrumental Analysis Center, Dalian University of Technology, 2 Linggong Road, Dalian 116024, P. R. of China

,

Jingping Qu

^bState Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, P. R. of China

,

Yuhan Zhou ∗

^aState Key Laboratory of Fine Chemicals, Department of Pharmaceutical Sciences, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, P. R. of China

› Author Affiliations

Abstract

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Abstract

A new strategy for the asymmetric allylic alkylation of azlactones with α-(trifluoromethyl)allyl acetates catalyzed by Pd(OAc)₂/(R)-BINAP is designed and developed, providing access to unsaturated α-quaternary α-amino acid derivatives bearing a trifluoromethyl group and contiguous quaternary and tertiary stereogenic centers. The products are obtained in good yields with exclusive regioselectivity and excellent stereoselective control under relatively mild reaction conditions. A scale-up experiment shows no loss of reactivity or stereoselectivity. The synthetic utility of the current strategy is demonstrated through transformations of a representative product to afford several potentially bioactive species.

Key words

palladium catalysis - trifluoromethyl alkylation - asymmetric catalysis - azlactones - α-(trifluoromethyl)allyl acetates

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References

References

1a Lee JH, Lee S.-g. Chem. Sci. 2013; 4: 2922
1b Bucci R, Giofré S, Clerici F, Contini A, Pinto A, Erba E, Soave R, Pellegrino S, Gelmi ML. J. Org. Chem. 2018; 83: 11493
1c De Marco R, Zhao J, Greco A, Ioannone S, Gentilucci L. J. Org. Chem. 2019; 84: 4992
1d Kobayashi M, Onozawa N, Matsuda K, Wakimoto T. Commun. Chem. 2024; 7: 67

For reviews, see:

2a Ohfune Y, Shinada T. Eur. J. Org. Chem. 2005; 5127
2b Tanaka M. Chem. Pharm. Bull. 2007; 55: 349
2c Metz AE, Kozlowski MC. J. Org. Chem. 2015; 80: 1
2d Appavoo SD, Huh S, Diaz DB, Yudin AK. Chem. Rev. 2019; 119: 9724

For some examples, see:

2e Polinelli S, Broxterman QB, Schoemaker HE, Boesten WH. J, Crisma M, Valle G, Toniolo C, Kamphuis J. Bioorg. Med. Chem. Lett. 1992; 2: 453
2f Toniolo C, Crisma M, Formaggio F, Peggion C. Biopolymers 2001; 60: 396
2g Wu HM, Zhang Z, Xiao F, Wei L, Dong XQ, Wang CJ. Org. Lett. 2020; 22: 4852
2h Lu B, Liang X, Zhang J, Wang Z, Peng Q, Wang X. J. Am. Chem. Soc. 2021; 143: 11799
2i Talbot FJ. T, Zhang S, Satpathi B, Howell GP, Perry GJ. P, Crisenza GE. M, Procter DJ. ACS Catal. 2021; 11: 14448
2j Torregrosa-Chinillach A, Carral-Menoyo A, Gomez-Bengoa E, Chinchilla R. J. Org. Chem. 2022; 87: 14507
2k Babawale F, Murugesan K, Narobe R, König B. Org. Lett. 2022; 24: 4793

3a For an example, see: Fustero S, Sanchez-Rosello M, Baez C, Del Pozo C, Garcia Ruano JL, Aleman J, Marzo L, Parra A. Amino Acids 2011; 41: 559

For reviews, see:

3b Venkatraman J, Shankaramma SC, Balaram P. Chem. Rev. 2001; 101: 3131
3c Najera C, Sansano JM. Chem. Rev. 2007; 107: 4584
3d Vogt H, Brase S. Org. Biomol. Chem. 2007; 5: 406
3e Arrayas RG, Carretero JC. Chem. Soc. Rev. 2009; 38: 1940
3f Liu WX, Wang R. Med. Res. Rev. 2011; 32: 536
3g Bera K, Namboothiri IN. N. Asian J. Org. Chem. 2014; 3: 1234
3h Noisier AF, Brimble MA. Chem. Rev. 2014; 114: 8775
3i Boibessot T, Benimelis D, Meffre P, Benfodda Z. Amino Acids 2016; 48: 2081

For reviews, see:

4a Fisk JS, Mosey RA, Tepe JJ. Chem. Soc. Rev. 2007; 36: 1432
4b de Castro PP, Carpanez AG, Amarante GW. Chem. Eur. J. 2016; 22: 10294
4c Yu X.-Y, Zhou F, Xiao W.-J, Chen J.-R. Curr. Catal. 2017; 6: 155
4d Marra IF. S, de Castro PP, Amarante GW. Eur. J. Org. Chem. 2019; 5830

For some examples, see:

4e Trost BM, Ariza X. J. Am. Chem. Soc. 1999; 121: 10727
4f Ruan S, Lin X, Xie L, Lin L, Feng X, Liu X. Org. Chem. Front. 2018; 5: 32
4g Zhang Z, Xiao F, Wu H.-M, Dong X.-Q, Wang C.-J. Org. Lett. 2020; 22: 569
4h Cheng X, Shen C, Dong X.-Q, Wang C.-J. Chem. Commun. 2022; 58: 3142
4i Zhou S.-S, Sun X.-Y, Liu W.-K, Song J.-Y, Wang Z, Qi Z.-H, Wang X.-W. J. Org. Chem. 2023; 88: 11867

5a Ooi T, Uraguchi D, Asai Y, Seto Y. Synlett 2009; 658
5b Uraguchi D, Asai Y, Ooi T. Angew. Chem. Int. Ed. 2009; 48: 733
5c Alba AN. R, Calbet T, Font-Bardía M, Moyano A, Rios R. Eur. J. Org. Chem. 2011; 2053
5d Tarí S, Avila A, Chinchilla R, Nájera C. Tetrahedron: Asymmetry 2012; 23: 176
5e Jeong B.-S, Lee Y.-J, Seo J, Kim D.-G, Park H.-g. Synlett 2013; 24: 701
5f Yan J, Chen M, Sung HH, Williams ID, Sun J. Chem. Asian J. 2018; 13: 2440

6a Cabrera S, Reyes E, Aleman J, Milelli A, Kobbelgaard S, Jorgensen KA. J. Am. Chem. Soc. 2008; 130: 12031
6b Balaguer AN, Companyó X, Calvet T, Font-Bardía M, Moyano A, Rios R. Eur. J. Org. Chem. 2009; 199
6c Hayashi Y, Obi K, Ohta Y, Okamura D, Ishikawa H. Chem. Asian J. 2009; 4: 246
6d Uraguchi D, Ueki Y, Ooi T. Science 2009; 326: 120
6e Uraguchi D, Ueki Y, Sugiyama A, Ooi T. Chem. Sci. 2013; 4: 1308
6f Liu Q, Qiao B, Chin KF, Tan CH, Jiang Z. Adv. Synth. Catal. 2014; 356: 3777

7a Uraguchi D, Ueki Y, Ooi T. J. Am. Chem. Soc. 2008; 130: 14088
7b Liu X, Deng L, Jiang X, Yan W, Liu C, Wang R. Org. Lett. 2010; 12: 876

8a Melhado AD, Luparia M, Toste FD. J. Am. Chem. Soc. 2007; 129: 12638
8b Dong S, Liu X, Chen X, Mei F, Zhang Y, Gao B, Lin L, Feng X. J. Am. Chem. Soc. 2010; 132: 10650
8c Ma C, Zhou JY, Zhang YZ, Mei GJ, Shi F. Angew. Chem. Int. Ed. 2018; 57: 5398

9a Kuwano R, Kondo Y. Org. Lett. 2004; 6: 3545
9b Trost BM, Czabaniuk LC. J. Am. Chem. Soc. 2012; 134: 5778
9c Trost BM, Czabaniuk LC. Chem. Eur. J. 2013; 19: 15210

10a Wang TC, Han ZY, Wang PS, Lin HC, Luo SW, Gong LZ. Org. Lett. 2018; 20: 4740
10b Lin HC, Xie PP, Dai ZY, Zhang SQ, Wang PS, Chen YG, Wang TC, Hong X, Gong LZ. J. Am. Chem. Soc. 2019; 141: 5824
10c Yang H, Xing D. Chem. Commun. 2020; 56: 3721
10d Zhang W.-N, Hu Y.-C, Liu Y, Wang X.-Y, Zhao Y.-Y, Chen Q.-A. Cell Rep. Phys. Sci. 2024; 5: 101908

11a Trost BM, Heinemann C, Ariza X, Weigand S. J. Am. Chem. Soc. 1999; 121: 8667
11b Trost BM, Ariza X. J. Am. Chem. Soc. 1999; 121: 10727
11c Trost BM, Dogra K. J. Am. Chem. Soc. 2002; 124: 7256
11d Trost BM, Ariza X. Angew. Chem. Int. Ed. 2003; 36: 2635
11e Kawatsura M, Tsuji H, Uchida K, Itoh T. Tetrahedron 2011; 67: 7686
11f Chen W, Hartwig JF. J. Am. Chem. Soc. 2013; 135: 2068
11g Chen W, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 377
11h Zhou H, Yang H, Liu M, Xia C, Jiang G. Org. Lett. 2014; 16: 5350
11i Wei X, Liu D, An Q, Zhang W. Org. Lett. 2015; 17: 5768
11j Bai XD, Zhang QF, He Y. Chem. Commun. 2019; 55: 5547
11k Zhou H, Yang H, Yin H, Liu M, Xia C, Jiang G. RSC Adv. 2014; 4: 25596

For reviews, see:

12a Bohm HJ, Banner D, Bendels S, Kansy M, Kuhn B, Muller K, Obst-Sander U, Stahl M. ChemBioChem 2004; 5: 637
12b Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
12c Hagmann WK. J. Med. Chem. 2008; 51: 4359

13 For a review, see: Jeschke P. ChemBioChem 2004; 5: 570
14 For a review, see: Berger R, Resnati G, Metrangolo P, Weber E, Hulliger J. Chem. Soc. Rev. 2011; 40: 3496

For reviews, see:

15a Qiu X.-L, Meng W.-D, Qing F.-L. Tetrahedron 2004; 60: 6711
15b Ulrich AS. Prog. Nucl. Magn. Reson. Spectrosc. 2005; 46: 1
15c Smits R, Cadicamo CD, Burger K, Koksch B. Chem. Soc. Rev. 2008; 37: 1727
15d Kitevski-LeBlanc JL, Prosser RS. Prog. Nucl. Magn. Reson. Spectrosc. 2012; 62: 1
15e Moschner J, Stulberg V, Fernandes R, Huhmann S, Leppkes J, Koksch B. Chem. Rev. 2019; 119: 10718

For some examples, see:

15f Zhu CL, Yang LJ, Li S, Zheng Y, Ma JA. Org. Lett. 2015; 17: 3442
15g Philippova AN, Vorobyeva DV, Monnier F, Osipov SN. Org. Biomol. Chem. 2020; 18: 3274

16a Zhao Y, Zhou Y, Liu J, Yang D, Tao L, Liu Y, Dong X, Liu J, Qu J. J. Org. Chem. 2016; 81: 4797
16b Zhao Y, Zhou Y, Zhang C, Wang H, Zhao J, Jin K, Liu J, Liu J, Qu J. Org. Biomol. Chem. 2017; 15: 5693
16c Li D, Zhou Y, Zhao Y, Zhang C, Li J, Zhao J, Qu J. J. Fluorine Chem. 2018; 212: 122
16d Zhao Y, Zhou Y, Zhang C, Li D, Sun P, Li J, Wang H, Liu J, Qu J. J. Org. Chem. 2018; 83: 2858
16e Zhou Y, Zhang C, Zhao Y, Li D, Zhao J, Wang Z, Qu J. Eur. J. Org. Chem. 2018; 6217
16f Li D, Lv S, Qu J, Zhou Y. Synthesis 2020; 52: 1203
16g Zhang C, Li D, Zhao Y, Zhao J, Qu J, Zhou Y. ChemistrySelect 2020; 5: 13099
16h Li D, Zhang W, Zhang S, Sun W, Zhao J, Wang B, Qu J, Zhou Y. Org. Lett. 2021; 23: 5804
16i Li D, Zhang S, Wang B, Sun W, Zhao J, Qu J, Zhou Y. Org. Chem. Front. 2022; 9: 810
16j Zhang S, Li D, Wang B, Sun W, Ma H, Di K, Sun L, Zhao J, Qu J, Zhou Y. Eur. J. Org. Chem. 2023; 26: e202300593
16k Cai N, Gao X, Yang L, Li W, Sun W, Zhang S, Zhao J, Qu J, Zhou Y. Eur. J. Med. Chem. 2024; 267: 116176
16l Cai N, Gao X, Li W, Yang L, Zhao J, Qu J, Zhou Y. Bioorg. Chem. 2024; 148: 107453

17a Kawatsura M, Terasaki S, Minakawa M, Hirakawa T, Ikeda K, Itoh T. Org. Lett. 2014; 16: 2442
17b Zhou M, Zhang J, Zhang X.-G, Zhang X. Org. Lett. 2019; 21: 671

18 Sicignano M, Rodríguez RI, Capaccio V, Borello F, Cano R, De Riccardis F, Bernardi L, Díaz-Tendero S, Della Sala G, Alemán J. Org. Biomol. Chem. 2020; 18: 2914

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