Enantioselective conjugate addition of ketones to nitroalkenes catalyzed by pyrrolidine-sulfamides

Chirality

Volumn 24, Issue 3, 2012, Pages 232-238

  Wang, Jinjia ^a   Lao, Jinhua ^a   Du, Quansheng ^a   Nie, Shaozhen ^a   Hu, Zhipeng ^a   Yan, Ming ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

asymmetric conjugate addition; chiral pyrrolidine sulfamide; ketone; nitroalkene; organocatalysis

Indexed keywords

BENZOIC ACID; CYCLOHEXANONE; KETONE; PYRROLIDINE DERIVATIVE; SULFAMIDE DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CHEMICAL REACTION; CONJUGATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REACTION TIME;

ALKENES; AMIDES; CATALYSIS; KETONES; NITRO COMPOUNDS; PYRROLIDINES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 84862800781     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.21987     Document Type: Article

References (49)

1. Bertelsen S., Jørgensen KA. Organocatalysis-after the gold rush. Chem Soc Rev 2009; 36: 2178-2189.
2. Guillena G, Nájera C, Ramõn DJ. Enantioselective direct aldol reaction: the blossoming of modern organocatalysis. Tetrahedron: Asymmetry 2007; 18: 2249-2293. (Pubitemid 47576631)
3. Dalko PI. Enantioselective organocatalysis. Weinheim: Wiley-VCH; 2007.
4. Pellissier H. Asymmetric organocatalysis. Tetrahedron 2007; 63: 9267-9331. (Pubitemid 47202039)
5. Dondoni A, Massi A. Asymmetric organocatalysis: from infancy to adolescence. Angew Chem Int Ed Engl 2008; 47: 4638-4660.
6. List B. The ying and yang of asymmetric aminocatalysis. Chem Commun 2006: 819-824. (Pubitemid 43255797)
7. Barbas CF III. Organocatalysis lost: modern chemistry, ancient chemistry, and an unseen biosynthetic apparatus. Angew Chem Int Ed Engl 2008; 47: 42-47.
8. Melchiorre P, Marigo M, Carlone A, Bartoli G. Asymmetric aminocatalysis-gold rush in organic chemistry. Angew Chem Int Ed Engl 2008; 47: 6138-6171.
9. Connon SJ. Organocatalysis mediated by (thio)urea derivatives. Chem Eur J 2006; 12: 5418-5427. (Pubitemid 44106353)
10. Taylor MS, Jacobsen EN. Asymmetric catalysis by chiral hydrogen-bond donors. Angew Chem Int Ed Engl 2006; 45: 1520-1543. (Pubitemid 44109228)
11. Ishihara K, Sakakura A, Hatano M. Design of highly functional small-molecule catalysts and related reactions based on acid-base combination chemistry. Synlett 2007; 5: 686-702.
12. Schreiner PR. Metal-free organocatalysis through explicit hydrogen bonding interactions. Chem Soc Rev 2003; 32: 289-296. (Pubitemid 38333546)
13. Zhang ZG, Schreiner PR. (Thio)urea organocatalysis-what can be learnt from anion recognition? Chem Soc Rev 2009; 38: 1187-1198.
14. Yu XH, Wang W. Hydrogen-bond-mediated asymmetric catalysis. Chem Asian J 2008; 3: 516-532.
15. Doyle AG, Jacobsen EN. Small-molecule H-bond donors in asymmetric catalysis. Chem Rev 2007; 107: 5713-5743.
16. Zhang XJ, Liu SP, Li XM, Yan M, Chan ASC. Highly enantioselective conjugate addition of aldehydes to nitroolefins catalyzed by chiral bifunctional sulfamides. Chem Commun 2009; 7: 833-835.
17. Liu SP, Zhang XJ, Lao JH, Yan M. Asymmetric conjugate addition of ketone to nitroalkenes catalyzed by chiral bifunctional sulfamides. ARKIVOC 2009; 7: 268-280.
18. Lao JH, Zhang XJ, Wang JJ, Li XM, Yan M, Luo HB. The effect of hydrogen bond donors in asymmetric organocatalytic conjugate additions. Tetrahedron: Asymmetry 2009; 20: 2818-2822.
19. Berner OM, Tedeschi L, Enders D. Asymmetric Michael additions to nitroalkenes. Eur J Org Chem 2002; 1877.
20. Sulzer-Mossé S, Alexakis A. Chiral amines as organocatalysts for asymmetric conjugate addition to nitroolefins and vinyl sulfones via enamine activation. Chem Commun 2007; 3123-3135. (Pubitemid 47174095)
21. Clarke ML, Fuentes JA. Self-assembly of organocatalysts: fine-tuning organocatalytic reactions. Angew Chem Int Ed Engl 2007; 46: 930-933. (Pubitemid 46192049)
22. Almaşi D, Alonso DA, Gõmez-Bengoa E, Nagel Y, Nájera C. Asymmetric conjugate addition of ketones to β-nitrostyrenes by means of 1,2-amino-alcohol-derived prolinamides as bifunctional catalysts. Eur J Org Chem 2007; 14: 2328-2343.
23. Freund M, Schenker S, Tsogoeva SB. Enantioselective nitro-Michael reactions catalyzed by short peptides on water. Org Biomol Chem 2009; 7: 4279-4284.
24. Chen JR, Lai YY, Lu HH, Wang XF, Xiao WJ. Highly enantioselective desymmetrization of meso- and prochiral cyclic ketones via organocatalytic Michael reaction. Tetrahedron 2009; 65: 9238-9243.
25. Cao CL, Ye MC, Sun XL, Tang Y. Pyrrolidine-thiourea as a bifunctional organocatalyst: highly enantioselective Michael addition of cyclohexanone to nitroolefins. Org Lett 2006; 8: 2901-2904. (Pubitemid 44154391)
26. Shen ZX, Zhang YQ, Jiao CJ, Li B, Ding J, Zhang YW. Enantioselective and diastereoselective Michael addition of ketone/aldehyde to trans-nitroolefins catalyzed by a novel chiral pyrrolidine-thiourea. Chirality 2007; 19: 307-312. (Pubitemid 46659344)
27. Lu AD, Gao P, Wu Y, Wang YM, Zhou ZH, Tang CC. Highly enantio- and diastereoselective Michael addition of cyclohexanone to nitroolefins catalyzed by a chiral glucose-based bifunctional secondary amine-thiourea catalyst. Org Biomol Chem 2009; 7: 3141-3147.
28. Chen JR, Gao YJ, Zou YQ, Tan F, Fu L, Zhu XY, Xiao WJ. Novel thiourea-amine bifunctional catalysts for asymmetric conjugate addition of ketones/aldehydes to nitroalkenes: rational structural combination for high catalytic efficiency. Org Biomol Chem 2010; 8: 1275-1279.
29. Cao YJ, Lai YY, Wang X, Li YJ, Xiao WJ. Michael additions in water of ketones to nitroolefins catalyzed by readily tunable and bifunctional pyrrolidine-thiourea organocatalysts. Tetrahedron Lett 2007; 48: 21-24. (Pubitemid 44821295)
30. Wang W, Wang J, Li H. Direct, highly enantioselective pyrrolidine sulfonamide catalyzed Michael addition of aldehydes to nitrostyrenes. Angew Chem Int Ed Engl 2005; 44: 1369-1371. (Pubitemid 40343551)
31. Wang J, Li H, Lou B, Zu LS, Guo H, Wang W. Enantio- and diastereoselective Michael addition reactions of unmodified aldehydes and ketones with nitroolefins catalyzed by a pyrrolidine sulfonamide. Chem Eur J 2006; 12: 4321-4332. (Pubitemid 43829104)
32. Ni BK, Zhang QY, Headley AD. Functionalized chiral ionic liquid as recyclable organocatalyst for asymmetric Michael addition to nitrostyrenes. Green Chem 2007; 9: 737-739.
33. Zhang QY, Ni BK, Headley AD. Asymmetric Michael addition reactions of aldehydes with nitrostyrenes catalyzed by functionalized chiral ionic liquids. Tetrahedron 2008; 64: 5091-5097.
34. Ni BK, Zhang QY, Headley AD. Highly enantioselective Michael addition of ketones to nitroolefins catalyzed by (S)-pyrrolidine arenesulfonamide. Tetrahedron: Asymmetry 2007; 18: 1443-1447. (Pubitemid 47069921)
35. Ni BK, Zhang QY, Dhungana K, Headley AD. Ionic liquid-supported (ILS) (S)-pyrrolidine sulfonamide, a recyclable organocatalyst for the highly enantioselective Michael addition to nitroolefins. Org Lett 2009; 11: 1037-1040.
36. Wang C, Yu C, Liu CL, Peng YG. 4-Trifluoromethanesulfonamidyl prolinol tert-butyldiphenylsilyl ether as a highly efficient bifunctional organocatalyst for Michael addition of ketones and aldehydes to nitroolefins. Tetrahedron Lett 2009; 50: 2363-2366.
37. Mandal T, Zhao CG. Synthesis of prolinal dithioacetals as catalysts for the highly stereoselective Michael addition of ketones and aldehydes to β-nitrostyrenes. Tetrahedron Lett 2007; 48: 5803-5806. (Pubitemid 47068780)
38. Xu DQ, Wang LP, Luo SP, Wang YF, Zhang S, Xu ZY. 2-[(Imidazolylthio) methyl]pyrrolidine as a trifunctional organocatalyst for the highly asymmetric Michael addition of ketones to nitroolefins. Eur J Org Chem 2008; 6: 1049-1053.
39. Li PH, Wang L, Wang M, Zhang YC. Polymer-immobilized pyrrolidine-based chiral ionic liquids as recyclable organocatalysts for asymmetric Michael additions to nitrostyrenes under solvent-free reaction conditions. Eur J Org Chem 2008; 7: 1157-1160.
40. Ishii T, Fujioka S, Sekiguchi Y, Kotsuki H. A new class of chiral pyrrolidine-pyridine conjugate base catalysts for use in asymmetric Michael addition reaction. J Am Chem Soc 2004; 126: 9558-9559. (Pubitemid 39031040)
41. Tan B, Zeng XF, Lu YP, Chua PJ, Zhong GF. Rational design of organocatalyst: highly stereoselective Michael addition of cyclic ketones to nitroolefins. Org Lett 2009; 11: 1927-1930.
42. Vishnumaya, Singh VK. Highly enantioselective water-compatible organocatalyst for Michael reaction of ketones to nitroolefins. Org Lett 2007; 9: 1117-1119.
43. Chen HB, Wang Y, Wei SY, Sun J. L-Proline derived triamine as a highly stereoselective organocatalyst for asymmetric Michael addition of cyclohexanone to nitroolefins. Tetrahedron: Asymmetry 2007; 18: 1308-1312. (Pubitemid 47030899)
44. Luo SZ, Mi XL, Zhang L, Liu S, Xu H, Cheng JP. Functionalized chiral ionic liquids as highly efficient asymmetric organocatalysts for Michael addition to nitroolefins. Angew Chem Int Ed Engl 2006; 45: 3093-3097. (Pubitemid 44099025)
45. Mase N, Watanabe K, Yoda H, Takabe K, Tanaka F, Barbas CF III. Organocatalytic direct Michael reaction of ketones and aldehydes with β-nitrostyrene in brine. J Am Chem Soc 2006; 128: 4966-4967.
46. Pansare SV, Pandya K. Simple diamine- and triamine-protonic acid catalysts for the enantioselective Michael addition of cyclic ketones to nitroalkenes. J Am Chem Soc 2006; 128: 9624-9625. (Pubitemid 44147934)
47. Chen JR, Fu L, Zou YQ, Chang NJ, Rong J, Xiao WJ. Pyrrolidinyl-sulfamide derivatives as a new class of bifunctional organocatalysts for direct asymmetric Michael addition of cyclohexanone to nitroalkenes. Org Biomol Chem 2011; 9: 5280-5287.
48. Dubois GE, Stephenson RA. Sulfonylamine-mediated sulfamation of amines. A mild, high yield synthesis of sulfamic acid salts. J Org Chem 1980; 45: 5371-5373. (Pubitemid 11185859)
49. DuBois GE. Amination of aryl sulfamate esters. A convenient general synthesis of aliphatic sulfamides. J Org Chem 1980; 45: 5373-5375.