Bio-inspired Chiral Primary Amine Catalysis

Long Zhang; Sanzhong Luo

doi:10.1055/s-0031-129068

Synlett, Table of Contents

Synlett 2012; 23(11): 1575-1589
DOI: 10.1055/s-0031-129068

account

Bio-inspired Chiral Primary Amine Catalysis

Long Zhang

Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China, Fax: +86(10)62554449 Email: luosz@iccas.ac.cn

,

Sanzhong Luo*

Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China, Fax: +86(10)62554449 Email: luosz@iccas.ac.cn

› Author Affiliations

Abstract

All articles of this category

Abstract

The search for new catalysts with superior performance and broad applicability remains a central theme in asymmetric organocatalysis. Inspired by Nature as well as by numerous previous efforts, we have developed chiral primary–tertiary diamines as both functional and mechanistic enzyme mimics, showing unprecedented scope in enamine-aldol reactions and significant potential in the reactions of acroleins. Our endeavors focusing on this type of catalysts are summarized in this account.

1 Introduction

2 General Features of Primary–Tertiary Vicinal Diamine/TfOH; Multifunctional Catalysis

3 Asymmetric Supramolecular Primary Amine Catalysis; Roles of the Hydrophobic Cavity

4 Asymmetric Direct Aldol Reaction of Aliphatic Ketones

5 Asymmetric Direct Cross-Aldol Reaction of Aldehydes

6 Asymmetric Retro-Aldol and Transfer-Aldol Reactions

7 Iminium Catalysis with Chiral Primary–Tertiary Diamines

8 Bifunctional Catalysis of Primary–Tertiary Diamines in the Baylis–Hillman Reaction

9 Conclusion, Remarks, and Outlook

Key words

primary amines - organocatalysts - aldol reaction - enamines - iminium

Full Text

References

References
1 In Privileged Chiral Ligands and Catalysts . Zhou Q.-L. Wiley-VCH; Weinheim: 2011

2a Berkessel A, Gröger H. Asymmetric Organocatalysis . Wiley-VCH; Weinheim: 2005
2b For recent reviews on aminocatalysis, see: Mukherjee S, Yang JW, Hoffmann S, List B. Chem. Rev. 2007; 107: 5471
2c See also: Erkkila A, Majander I, Pihko PM. Chem. Rev. 2007; 107: 5416

3 For our other efforts along this line, see: Luo S, Zhang L, Cheng J.-P. Chem. Asian J. 2009; 4: 1184

For reviews on primary amine catalysts, see:

4a Peng F, Shao Z. J. Mol. Catal. A: Chem. 2008; 285: 1
4b Xu L.-W, Luo J, Lu Y. Chem. Commun. 2009; 1807
4c Xu L.-W, Lu Y. Org. Biomol. Chem. 2008; 6: 2047
4d Chen Y.-C. Synlett 2008; 1919
4e Bartoli G, Melchiorre P. Synlett 2008; 1759

5a Gefflaut T, Blonksi C, Perie J, Willson M. Prog. Biophys. Molec. Biol. 1995; 63: 301
5b Gijsen HJ. M, Qiao L, Fitz W, Wong C.-H. Chem. Rev. 1996; 96: 443

6a Harada N, Sugioka T, Uda H, Kuriki T. Synthesis 1990; 53
6b Clemente FR, Houk KN. J. Am. Chem. Soc. 2005; 127: 11294 ; and references therein
6c Mander LN, Turner JV. Tetrahedron Lett. 1981; 22: 3683
6d Hagiwara H, Uda H. J. Org. Chem. 1988; 53: 2308

7a Ibrahem I, Zou W, Engqvist M, Xu Y, Córdova A. Chem. Eur. J. 2005; 11: 7024
7b Córdova A, Zou WB, Ibrahem I, Reyes E, Engqvist M, Liao WW. Chem. Commun. 2005; 3586

8 Tsogoeva SB, Wei S. Chem. Commun. 2006; 1451
9 Huang H, Jacobsen EN. J. Am. Chem. Soc. 2006; 128: 7170
10 Ramasastry SS. V, Zhang H, Tanaka F, Barbas CF. III. J. Am. Chem. Soc. 2007; 129: 288

11a Xu X.-Y, Wang Y.-Z, Gong L.-Z. Org. Lett. 2007; 9: 4247
11b Li J, Yang Z, Wang Z, Wang F, Chen X, Liu X, Feng X.-M. J. Am. Chem. Soc. 2008; 130: 5654
11c Wu X, Ma Z, Ye Z, Qian S, Zhao G. Adv. Synth. Catal. 2009; 351: 158

12a Westheimer FH. Tetrahedron 1995; 51: 3
12b Heine A, DeSantis G, Luz JG, Mitchell M, Wong C.-H, Wilson IA. Science 2001; 294: 369

13a Barbas CF. III, Heine A, Zhong G, Hoffmann T, Gramatikova S, Bjornestedt R, List B, Anderson J, Stura EA, Wilson IA, Lerner RA. Science 1997; 278: 2085
13b Ho M.-C, Menetret J.-F, Tsuruta H, Allen KN. Nature 2009; 459: 393

14 Hine J. Acc. Chem. Res. 1978; 11: 1
15 For a recent discussion, see: Saito S, Yamamoto H. Acc. Chem. Res. 2004; 37: 570
16 Luo S, Xu H, Li J, Zhang L, Cheng J.-P. J. Am. Chem. Soc. 2007; 129: 3074
17 Li J, Xu H, Xue X, Luo S, Cheng J.-P unpublished results
18 Hu S, Li J, Xiang J, Pan J, Luo S, Cheng J.-P. J. Am. Chem. Soc. 2010; 132: 7216

For reviews on enzyme mimics based on cyclodextrin, see:

19a Breslow R, Dong SD. Chem. Rev. 1998; 98: 1997
19b Rekharsky MV, Inoue Y. Chem. Rev. 1998; 98: 1875

20a Breslow R, Graff A. J. Am. Chem. Soc. 1993; 115: 10988
20b Desper JM, Breslow R. J. Am. Chem. Soc. 1994; 116: 12081

21a Brogan AP, Dickerson TJ, Janda KD. Angew. Chem. Int. Ed. 2006; 45: 8100
21b Hayashi Y. Angew. Chem. Int. Ed. 2006; 45: 8103
21c Blackmond DG, Armstrong A, Coombe V, Wells A. Angew. Chem. Int. Ed. 2007; 46: 3798

22 Trost BM, Brindle CS. Chem. Soc. Rev. 2010; 39: 1600
23 Li J, Luo S, Cheng J.-P. J. Org. Chem. 2009; 74: 1747

24a Enders D, Voith M, Lenzen A. Angew. Chem. Int. Ed. 2005; 44: 1304
24b Wong C.-H, Machajewski TD. Angew. Chem. Int. Ed. 2000; 39: 1352

25a For a selected example, see: Enders D, Grondal C. Angew. Chem. Int. Ed. 2005; 44: 1210
25b For syn-selective aldol reaction of protected dihydroxyacetones, see: Utsumi N, Imai M, Tanaka F, Ramasastry S.s.V, Barbas CF. III. Org. Lett. 2007; 9: 3445

For direct aldol reaction of free DHA with low stereoselectivity or racemic products, see:

26a Córdova A, Notz W, Barbas CF. III. Chem. Commun. 2002; 3024
26b Market M, Mulzer M, Schetter B, Mahrwald R. J. Am. Chem. Soc. 2007; 129: 7258
26c Kofoed J, Darbre T, Reymond J.-L. Chem. Commun. 2006; 1482
26d For a successful syn-aldol reaction of free dihydroxyacetone, see: Ramasastry SS. V, Albertshofer K, Utsumi N, Tanaka F, Barbas CF. III. Angew. Chem. Int. Ed. 2007; 46: 5572

27 Luo S, Xu H, Zhang L, Li J, Cheng J.-P. Org. Lett. 2008; 10: 653

28a Angata T, Varki A. Chem. Rev. 2002; 102: 439
28b Wong C.-H In Enzymes in Synthetic Organic Chemistry . Wong C.-H, Whitesides GM. Elsevier; Oxford: 1994: 215-219

29a Enders D, Gasperi T. Chem. Commun. 2007; 88
29b Schetter B, Mahrwald R. Angew. Chem. Int. Ed. 2006; 45: 7506

30 Luo S, Xu H, Chen L, Cheng J.-P. Org. Lett. 2008; 10: 1774
31 Denmark SE, Heemstra JR, Beutner GL. Angew. Chem. Int. Ed. 2005; 44: 4682
32 Luo S, Qiao Y, Zhang L, Li J, Li X, Cheng J.-P. J. Org. Chem. 2009; 74: 9521
33 Qiao Y. Ph.D. Thesis. Institute of Chemistry, The Chinese Academy of Sciences; P. R. of China: 2011

34a Eder U, Sauer G, Wiechert R. Angew. Chem. Int. Ed. Engl. 1971; 10: 496 Angew. Chem. 1971; 83 492
34b Hajos ZG, Parrish DR. J. Org. Chem. 1973; 38: 3239
34c Hajos ZG, Parrish DR. J. Org. Chem. 1974; 39: 1615

35 Bradshaw B, Etxebarria-Jardi G, Bonjoch J, Viozquez SF, Guillena G, Najera C. Adv. Synth. Catal. 2009; 351: 2482
36 Zhou P, Zhang L, Luo S, Cheng J.-P. J. Org. Chem. 2012; 77: 2526

For a review, see:

37a Zhang L, Luo S, Cheng J.-P. Catal. Sci. Technol. 2011; 1: 507
37b Luo S, Li J, Zhang L, Xu H, Cheng J.-P. Chem. Eur. J. 2008; 14: 1273

38 Luo S, Zheng X, Cheng J.-P. Chem. Commun. 2008; 5719

39a Scheffler U, Mahrwald R. Synlett 2011; 1660
39b Market M, Scheffler U, Mahrwald R. J. Am. Chem. Soc. 2009; 131: 16642

40a Kano T, Yamaguchi Y, Tanaka Y, Maruoka K. Angew. Chem. Int. Ed. 2007; 46: 1738
40b Kano T, Yamaguchi Y, Maruoka K. Chem. Eur. J. 2009; 15: 6678

41 Li J, Fu N, Li X, Luo S, Cheng J.-P. J. Org. Chem. 2010; 75: 4501
42 For reviews on organocatalytic reactions with acetaldehyde, see: Alcaide B, Almendros P. Angew. Chem. Int. Ed. 2008; 47: 4632
43 For an example, see: Hayashi Y, Itoh T, Aratake S, Ishikawa H. Angew. Chem. Int. Ed. 2008; 47: 2082
44 Hu S, Zhang L, Li J, Luo S, Cheng J.-P. Eur. J. Org. Chem. 2011; 3347

45a Flanagan ME, Jacobsen JR, Sweet E, Schultz PG. J. Am. Chem. Soc. 1996; 118: 6078
45b Zhong GF, Shabat D, List B, Anderson J, Sinha SC, Lerner RA, Barbas CF. III. Angew. Chem. Int. Ed. 1998; 37: 2481

46a Tosaki SY, Hara K, Gnanadesikan V, Morimoto H, Harada S, Sugita M, Yamagiwa N, Matsunaga S, Shibasaki M. J. Am. Chem. Soc. 2006; 128: 11776
46b Hara K, Tosaki SY, Gnanadesikan V, Morimoto H, Harada S, Sugita M, Yamagiwa N, Matsunaga S, Shibasaki M. Tetrahedron 2009; 65: 5030

47 Luo S, Zhou P, Li J, Cheng J.-P. Chem. Eur. J. 2010; 16: 4457
48 Zhou P, Luo S, Cheng J.-P. Org. Biomol. Chem. 2011; 9: 1784

49a Ishihara K, Nakano K. J. Am. Chem. Soc. 2005; 127: 10504
49b Sakakura A, Suzuki K, Nakano K, Ishihara K. Org. Lett. 2006; 8: 2229
49c Sakakura A, Suzuki K, Ishihara K. Adv. Synth. Catal. 2006; 348: 2457
49d Ishihara K, Nakano K, Akakura M. Org. Lett. 2008; 10: 2893
49e Ishihara K, Nakano K. J. Am. Chem. Soc. 2007; 129: 8930

50 Kano T, Tanaka Y, Osawa K, Yurino T, Maruoka K. Chem. Commun. 2009; 1956
51 Lifchits O, Reisinger CM, List B. J. Am. Chem. Soc. 2010; 132: 10227
52 Erkkila A, Pihko PM, Clark M.-R. Adv. Synth. Catal. 2007; 349: 802
53 Li J, Li X, Zhou P, Zhang L, Luo S, Cheng J.-P. Eur. J. Org. Chem. 2009; 4486
54 Li J, Fu N, Zhang L, Zhou P, Luo S, Cheng J.-P. Eur. J. Org. Chem. 2010; 6840
55 Bondzic BP, Urushima T, Ishikawa H, Hayashi Y. Org. Lett. 2010; 12: 5434
56 Fu N, Zhang L, Li J, Luo S, Cheng J.-P. Angew. Chem. Int. Ed. 2011; 50: 11451
57 Mohr JT, Hong AY, Stoltz BM. Nat. Chem. 2009; 1: 359
58 Zhang L, Luo SZ, Chen LJ, Li J, Cheng J.-P. Sci. China, Ser. B: Chem. 2009; 52: 1300
59 Gruttadauria M, Giacalone F, Paolo Lo Meo P, Marculescu AM, Riela S, Noto R. Eur. J. Org. Chem. 2008; 1589