Organocatalytic asymmetric Michael addition of 2,4-pentandione to nitroolefins

被引:247
作者
Wang, J [1 ]
Li, H
Duan, WH
Zu, LS
Wang, W
机构
[1] Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA
[2] Chinese Acad Sci, Shanghai Inst Biol Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
关键词
D O I
10.1021/ol0519137
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel binaphthyl-derived amine thiourea organocatalyst has been developed and demonstrated to efficiently catalyze Michael addition reactions (using as low as 1 mol % loading) of diketones to nitroalkenes with remarkably high enantioselectivities.
引用
收藏
页码:4713 / 4716
页数:4
相关论文
共 48 条
[11]   A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids [J].
Córdova, A ;
Notz, W ;
Zhong, GF ;
Betancort, JM ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1842-1843
[12]   Conformational analysis and stereochemical assignments of products derived from C-H activation at secondary sites [J].
Davies, HML ;
Ren, PD .
TETRAHEDRON LETTERS, 2001, 42 (18) :3149-3151
[13]  
Enders D, 2002, SYNLETT, P26
[14]   Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes [J].
Hayashi, Y ;
Gotoh, H ;
Hayashi, T ;
Shoji, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (27) :4212-4215
[15]   Enantioselective Michael addition to α,β-unsaturated imides catalyzed by a bifunctional organocatalyst [J].
Hoashi, Y ;
Okino, T ;
Takemoto, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) :4032-4035
[16]   A new class of chiral pyrrolidine-pyridine conjugate base catalysts for use in asymmetric Michael addition reactions [J].
Ishii, T ;
Fujioka, S ;
Sekiguchi, Y ;
Kotsuki, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) :9558-9559
[17]   Catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes [J].
Ji, JG ;
Barnes, DM ;
Zhang, J ;
King, SA ;
Wittenberger, SJ ;
Morton, HE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) :10215-10216
[18]   Asymmetric carbon-carbon bond formations in conjugate additions of lithiated N-boc allylic and benzylic amines to nitroalkenes:: Enantioselective synthesis of substituted piperidines, pyrrolidines, and pyrimidinones [J].
Johnson, TA ;
Jang, DO ;
Slafer, BW ;
Curtis, MD ;
Beak, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11689-11698
[19]   Thiourea-catalyzed enantioselective hydrophosphonylation of imines:: Practical access to enantiomerically enriched α-amino phosphonic acids [J].
Joly, GD ;
Jacobsen, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4102-4103
[20]   ASYMMETRIC ADDITION OF THIOGLYCOLIC ACID TO NITRO OLEFINS CATALYZED BY CINCHONA ALKALOIDS [J].
KOBAYASHI, N ;
IWAI, K .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (09) :1823-1828