Recent Advances in Chiral Aldehyde Catalysis for Asymmetric Functionalization of Amines

Abstract

Asymmetric functionalization of amines and their derivatives is of great significance in synthetic chemistry and is widely used in the preparation of natural products and pharmaceuticals. In recent years, chiral aldehyde catalysis has emerged as a well-established and recognized tool, providing excellent catalytic activation and stereoselective control in asymmetric reactions of N-unprotected amino acid esters and amino acid ester analogues. In this short review, recent advances in enantioselective aldehyde catalysis, including chiral aldehydes as organocatalysts and co-catalysis combined with transition metals, will be summarized. Lastly, continued development of enantioselective aldehyde catalysis is prospected in the future.

1 Introduction

2 Chiral Aldehyde Catalysis for Tethering Strategy

3 Chiral Aldehyde Catalysis for Imine Activation

4 Chiral Aldehyde/Transition Metal Cooperative Catalysis

5 Conclusion

Key words

asymmetric catalysis - organocatalysis - chiral aldehyde catalysis - asymmetric functionalization - amines - amino acids

Publication History

Received: 06 October 2022

Accepted after revision: 07 November 2022

Accepted Manuscript online:
07 November 2022

Article published online:
30 November 2022

• References

• 1a Chiral Amine Synthesis: Methods, Developments and Applications. Nugent TC. Wiley-VCH; Weinheim: 2010
• 1b Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257
• 2a Non-natural Amino Acids:Methods and Protocols . Pollegioni L, Servi S. Springer; New York: 2012
• 2b Amino Acids, Peptides and Proteins in Organic Chemistry. Hughes AB. Wiley-VCH; Weinheim: 2009
• 2c Sourkes TL. Arch. Biochem. Biophys. 1954; 51: 444
• 2d Farsello D, Giartosio A, Hammes GG. Biochemistry 1966; 5: 197
• 2e Schirlin D, Gerhart F, Hornsperger JM, Hamon M, Wagner J, Jung MJ. J. Med. Chem. 1988; 31: 30
• 3a Asymmetric Organocatalysis . In Topics in Current Chemistry, Vol. 291. List B. Springer; Heidelberg: 2009
• 3b Stereoselective Organocatalysis: Bond Formation Methodologies and Activation Modes. Torres RR. Wiley; Hoboken: 2013
• 3c Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications. Dalko PI. Wiley-VCH; Weinheim: 2013
• 4 Mukherjee S, Yang JW, Hoffmann S, List B. Chem. Rev. 2007; 107: 5471
• 5 Lelais G, MacMillan DW. C. Aldrichimica Acta 2006; 39: 79
• 6a Akiyama T. Chem. Rev. 2007; 107: 5744
• 6b Doyle AG, Jacobsen EN. Chem. Rev. 2007; 107: 5713
• 6c Parmar D, Sugiono E, Raja S, Rueping M. Chem. Rev. 2014; 114: 9047
• 6d Taylor MS, Jacobsen EN. Angew. Chem. Int. Ed. 2006; 45: 1520
• 7 Tian S.-K, Chen Y, Hang J, Tang L, McDaid P, Deng L. Acc. Chem. Res. 2004; 37: 621
• 8a Ryan SJ, Candish L, Lupton DW. Chem. Soc. Rev. 2013; 42: 4906
• 8b Enders D, Niemeier O, Henseler A. Chem. Rev. 2007; 107: 5606
• 9a Shirakawa S, Maruoka K. Angew. Chem. Int. Ed. 2013; 52: 4312
• 9b Ooi T, Maruoka K. Angew. Chem. Int. Ed. 2007; 46: 4222
• 10 Wang Q, Gu Q, You S.-L. Angew. Chem. Int. Ed. 2019; 58: 6818
• 11a O’Donnell MJ. Acc. Chem. Res. 2004; 37: 506
• 11b Lygo B, Andrews BI. Acc. Chem. Res. 2004; 37: 518
• 11c Hashimoto T, Maruoka K. Chem. Rev. 2007; 107: 5656
• 11d Maruoka K, Ooi T, Kano T. Chem. Commun. 2007; 1487
• 12a Wei L, Xu S.-M, Zhu Q, Che C, Wang C.-J. Angew. Chem. Int. Ed. 2017; 56: 12312
• 12b Huo X, He R, Fu J, Zhang J, Yang G, Zhang W. J. Am. Chem. Soc. 2017; 139: 9819
• 12c Wei L, Zhu Q, Xu S.-M, Chang X, Wang C.-J. J. Am. Chem. Soc. 2018; 140: 1508
• 12d Huo X, Zhang J, Fu J, He R, Zhang W. J. Am. Chem. Soc. 2018; 140: 2080
• 13a Bols M, Skrydstrup T. Chem. Rev. 1995; 95: 1253
• 13b Fensterbank L, Malacria M, Sieburth SMcN. Synthesis 1997; 813
• 13c Gauthier DR. Jr, Zandi KS, Shea KJ. Tetrahedron 1998; 54: 2289
• 13d Sugimura T. Eur. J. Org. Chem. 2004; 1185
• 13e Bracegirdle S, Anderson EA. Chem. Soc. Rev. 2010; 39: 4114
• 13f Čusak A. Chem. Eur. J. 2012; 18: 5800
• 13g Pascal R. Eur. J. Org. Chem. 2003; 1813
• 13h Tan KL. ACS Catal. 2011; 1: 877
• 14 Li B.-J, Ei-Nachef C, Beauchemin AM. Chem. Commun. 2017; 53: 13192
• 15a MacDonald MJ, Schipper DJ, Ng PJ, Moran J, Beauchemin AM. J. Am. Chem. Soc. 2011; 133: 20100
• 15b MacDonald MJ, Hesp CR, Schipper DJ, Pesant M, Beauchemin AM. Chem. Eur. J. 2013; 19: 2597
• 15c Guimond N, MacDonald MJ, Lemieux V, Beauchemin AM. J. Am. Chem. Soc. 2012; 134: 16571
• 16 Kuzuhara H, Watanabe N, Ando M. J. Chem. Soc., Chem. Commun. 1987; 95
• 17 Koh JT, Delaude L, Breslow R. J. Am. Chem. Soc. 1994; 116: 11234
• 18 Xu B, Shi L.-L, Zhang Y.-Z, Wu Z.-J, Fu L.-N, Luo C.-Q, Zhang L.-X, Peng Y.-G, Guo Q.-X. Chem. Sci. 2014; 5: 1988
• 19 Chen J, Gong X, Li J, Li Y, Ma J, Hou C, Zhao G, Yuan W, Zhao B. Science 2018; 360: 1438
• 20 Wen W, Chen L, Luo M.-J, Zhang Y, Chen Y.-C, Ouyang Q, Guo Q.-X. J. Am. Chem. Soc. 2018; 140: 9774
• 21 Liao G, Chen H.-M, Xia Y.-N, Li B, Yao Q.-J, Shi B.-F. Angew. Chem. Int. Ed. 2019; 58: 11464
• 22a Tian J.-M, Wang A.-F, Yang J.-S, Zhao X.-J, Tu Y.-Q, Zhang S.-Y, Chen Z.-M. Angew. Chem. Int. Ed. 2019; 58: 11023
• 22b Lv X, Xu J, Sun C, Su F, Cai Y, Jin Z, Chi YR. ACS Catal. 2022; 12: 2706
• 22c Wu Y, Li M, Sun J, Zheng G, Zhang Q. Angew. Chem. Int. Ed. 2022; 61: e202117340
• 22d Gao Q, Wu C, Deng S, Li L, Liu Z.-S, Hua Y, Ye J, Liu C, Cheng H.-G, Cong H, Jiao Y, Zhou Q. J. Am. Chem. Soc. 2021; 143: 7253
• 22e Liu Z.-S, Hua Y, Gao Q, Ma Y, Tang H, Shang Y, Cheng H.-G, Zhou Q. Nat. Catal. 2020; 3: 727
• 22f Zhang J, Xu Q, Fan J, Zhou L, Liu N, Zhu L, Wu J, Xie M. Org. Chem. Front. 2021; 8: 3404
• 22g Zhao W, Liu J, He X, Jiang H, Lu L, Xiao W. Chin. J. Org. Chem. 2022; 42: 2504
• 23 Ma J, Zhou Q, Song G, Song Y, Zhao G, Ding K, Zhao B. Angew. Chem. Int. Ed. 2021; 60: 10588
• 24 Wang W.-Z, Shen H.-R, Liao J, Wen W, Guo Q.-X. Org. Chem. Front. 2022; 9: 1422
• 25 Cheng A, Zhang L, Zhou Q, Liu T, Cao J, Zhao G, Zhang K, Song G, Zhao B. Angew. Chem. Int. Ed. 2021; 60: 20166
• 26 Ma J, Gao B, Song G, Zhang R, Wang Q, Ye Z, Chen W.-W, Zhao B. Angew. Chem. Int. Ed. 2022; 61: e202200850
• 27 Wen W, Luo M.-J, Yuan Y, Liu J.-H, Wu Z.-L, Cai T, Wu Z.-W, Ouyang Q, Guo Q.-X. Nat. Commun. 2020; 11: 5372
• 28 Ji P, Liu X, Xu J, Zhang X, Guo J, Chen W.-W, Zhao B. Angew. Chem. Int. Ed. 2022; 61: e202206111
• 29a Chen G.-S, Deng Y.-J, Gong L.-Z, Mi A.-Q, Cui X, Jiang Y.-Z, Choi MC. K, Chan AS. C. Tetrahedron: Asymmetry 2001; 12: 1567
• 29b Nakoji M, Kanayama T, Okino T, Takemoto Y. Org. Lett. 2001; 3: 3329
• 30a Shao Z, Zhang H. Chem. Soc. Rev. 2009; 38: 2745
• 30b Du Z, Shao Z. Chem. Soc. Rev. 2013; 42: 1337
• 30c Chen DF, Han ZY, Zhou XL, Gong LZ. Acc. Chem. Res. 2014; 47: 2365
• 30d Chen D.-F, Gong L.-Z. J. Am. Chem. Soc. 2022; 144: 2415
• 31 Chen L, Luo M.-J, Zhu F, Wen W, Guo Q.-X. J. Am. Chem. Soc. 2019; 141: 5159
• 32 Zhu F, Shen Q.-W, Wang W.-Z, Wu Z.-L, Cai T, Wen W, Guo Q.-X. Org. Lett. 2021; 23: 1463
• 33 Liu J.-H, Wen W, Liao J, Shen Q.-W, Lin Y, Wu Z.-L, Cai T, Guo Q.-X. Nat. Commun. 2022; 13: 2509 ; and references cited therein
• 34 Fang P, Chaulagain MR, Aron ZD. Org. Lett. 2012; 14: 2130
• 35 Zhong X, Zhong Z, Wu Z, Ye Z, Feng Y, Dong S, Liu X, Peng Q, Feng X. Chem. Sci. 2021; 12: 4353