β-aminosulfonamide-catalyzed direct asymmetric aldol reaction in brine

Synlett

Volumn , Issue 3, 2011, Pages 410-414

  Miura, Tsuyoshi ^a   Ina, Mariko ^a   Imai, Kie ^a   Nakashima, Kosuke ^a   Masuda, Akira ^a   Tada, Norihiro ^a   Imai, Nobuyuki ^b   Itoh, Akichika ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b CHIBA INSTITUTE OF SCIENCE   (Japan)

Author keywords

aldol reaction; asymmetric; brine; organocatalyst; sulfonamide

Indexed keywords

ACETIC ACID ETHYL ESTER; ACID ANHYDRIDE; ALDEHYDE; ANISALDEHYDE; BENZALDEHYDE DERIVATIVE; BETA AMINOSULFONAMIDE; CYCLOHEXANONE; DICHLOROMETHANE; HYDROCHLORIC ACID; KETONE; PHENYLALANINE; SULFONAMIDE; TRIETHYLAMINE; TRIFLUOROACETIC ACID; TRIFLUOROMETHANESULFONIC ACID; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG; WATER;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYST; CATALYST SUPPORT; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ORGANIC CHEMISTRY; PHASE TRANSITION; REACTION ANALYSIS; REACTION OPTIMIZATION; REACTION TIME; REDUCTION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SUSPENSION; TEMPERATURE SENSITIVITY; WATER ANALYSIS;

EID: 79551686994     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259317     Document Type: Article

References (41)

1. For selected reviews on organocatalysis, see:, Dalko P I., Moisan L, Angew. Chem. Int. Ed. 2004 43 5138
2. Pellissier H, Tetrahedron 2007 63 9267
3. Mukherjee S, Yang J W., Hoffmann S, List B, Chem. Rev. 2007 107 5471
4. Dondoni A, Massi A, Angew. Chem. Int. Ed. 2008 47 4638
5. Lattanzi A, Chem. Commun. 2009 1452
6. Liu X, Lin L, Feng X, Chem. Commun. 2009 6145
7. Modern Aldol Reactions Vol. 1 and 2 Mahrwald R Wiley-VCH Weinheim 2004
8. For selected reviews on organocatalysis in water, see
9. Gruttadauria M, Giacalone F, Noto R, Adv. Synth. Catal. 2009 351 33
10. Paradowska J, Stodulski M, Mlynarski J, Angew. Chem. Int. Ed. 2009 48 4288
11. Raj M, Singh K, Chem. Commun. 2009 6687
12. An Y.-J, Zhang Y.-X, Wu Y, Liu Z.-M, Pi C, Tao J.-C, Tetrahedron: Asymmetry 2010 21 688
13. Zhang S.-P, Fu X.-K, Fu S.-D, Tetrahedron Lett. 2009 50 1173
14. Zhou H, Xie Y, Ren L, Wang K, Adv. Synth. Catal. 2009 351 1284
15. Ma X, Da C S, Yi L, Jia Y.-N, Guo Q.-P, Che L.-P, Wu F.-C, Wang J.-R, Li W.-P, Tetrahedron: Asymmetry 2009 20 1419
16. Chimni S S., Singh S, Kumar A, Tetrahedron: Asymmetry 2009 20 1722
17. Fu S.-D, Fu X.-K, Zhang S.-P, Zou X.-C, Wu X.-J, Tetrahedron: Asymmetry 2009 20 2390
18. Vishnumaya M R., Singh V K., J. Org. Chem. 2009 74 4289
19. Nisco M D., Pedatella S, Ullah H, Zaidi J H., Naviglio D, Ozdamar O, Caputo R, J. Org. Chem. 2009 74 9562
20. Vishnumaya M R., Singh V K., J. Org. Chem. 2009 74 4289
21. Mase N, Noshiro N, Mokuya A, Takabe K, Adv. Synth. Catal. 2009 351 2791
22. Tea Y.-C, Lee P P., Synth. Commun. 2009 39 3081
23. Jia Y.-N, Wu F.-C, Ma X, Zhu G.-J, Da C S, Tetrahedron Lett. 2009 50 3059
24. Ramasastry S S. V., Albertshofer K, Utsumi N, Barbas C F., Org. Lett. 2008 10 1621
25. Zhu M.-K, Xu X.-Y, Gong L.-Z, Adv. Synth. Catal. 2008 350 1390
26. Zu L, Xie H, Li H, Wang J, Wang W, Org. Lett. 2008 10 1211
27. Gandhi S, Singh V K., J. Org. Chem. 2008 73 9411
28. Zhao J.-F, He L, Jiang J, Tang Z, Cun L.-F, Gong L.-Z, Tetrahedron Lett. 2008 49 3372
29. Huang W.-P, Chen J.-R, Li X.-Y, Cao Y.-J, Xiao W.-J, Can. J. Chem. 2007 85 208
30. Huang J, Zhang X, Armstrong D W., Angew. Chem. Int. Ed. 2007 46 9073
31. Gryko D, Saletra W J., Org. Biomol. Chem. 2007 5 2148
32. Hayashi Y, Sumiya T, Takahashi J, Gotoh H, Urushima T, Shoji M, Angew. Chem. Int. Ed. 2006 45 958
33. Mase N, Nakai Y, Ohara N, Yoda H, Takabe K, Tanaka F, Barbas C F., J. Am. Chem. Soc. 2006 128 734
34. Nakayama K, Maruoka K, J. Am. Chem. Soc. 2008 130 17666
35. Miura T, Yasaku Y, Koyata N, Murakami Y, Imai N, Tetrahedron Lett. 2009 50 2632
36. Miura T, Imai K, Ina M, Tada N, Imai N, Itoh A, Org. Lett. 2010 12 1620
37. Imai N, Nokami J, Nomura T, Ninomiya Y, Shinobe A, Matsushiro S, Bull. Okayama Univ. Sci. 2002 47
38. Bassan A, Zou W, Reues E, Himo F, Crdova A, Angew. Chem. Int. Ed. 2005 44 7028
39. Dziedzic P, Zou W, Hfren J, Crdova A, Org. Biomol. Chem. 2006 4 38
40. Mase N, Watanabe K, Yoda H, Takabe K, Tanaka F, Barbas C F., J. Am. Chem. Soc. 2006 128 4966
41. 0 see:, Maya V, Singh V K., Org. Lett. 2007 9 1117