Enantioselective bronsted acid catalyzed conjugate addition of aryl methyl ketone derived enamines to nitroalkenes

被引:24
作者
Dixon, DJ
Richardson, RD
机构
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
[2] Univ Cambridge, Chem Labs, Cambridge CB2 1EW, England
关键词
Bronsted acid; organocatalysis; nitroalkene; thiourea; enantioselective;
D O I
10.1055/s-2005-922776
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel Bronsted acid catalyst has been developed for the conjugate addition of aryl methyl ketone derived enamines to nitroalkenes in good yield and moderate enantioselectivity.
引用
收藏
页码:81 / 85
页数:5
相关论文
共 48 条
[1]   Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].
Akiyama, T ;
Itoh, J ;
Yokota, K ;
Fuchibe, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568
[2]   Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].
Alexakis, A ;
Andrey, O .
ORGANIC LETTERS, 2002, 4 (21) :3611-3614
[3]   Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results [J].
Ballini, R ;
Bosica, G ;
Fiorini, D ;
Palmieri, A ;
Petrini, M .
CHEMICAL REVIEWS, 2005, 105 (03) :933-971
[4]  
Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[5]   Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins [J].
Betancort, JM ;
Sakthivel, K ;
Thayumanavan, R ;
Tanaka, F ;
Barbas, CF .
SYNTHESIS-STUTTGART, 2004, (09) :1509-1521
[6]   Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].
Betancort, JM ;
Barbas, CF .
ORGANIC LETTERS, 2001, 3 (23) :3737-3740
[7]   Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates [J].
Betancort, JM ;
Sakthivel, K ;
Thayumanavan, R ;
Barbas, CF .
TETRAHEDRON LETTERS, 2001, 42 (27) :4441-4444
[8]   ASYMMETRIC MICHAEL-ADDITIONS - PRACTICALLY COMPLETELY DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ALKYLATIONS OF THE ENAMINE FROM CYCLOHEXANONE AND PROLINYL METHYL-ETHER BY OMEGA-NITROSTYRENES TO GIVE U- 2-(1'-ARYL-2'-NITROETHYL)CYCLOHEXANONES [J].
BLARER, SJ ;
SCHWEIZER, WB ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1982, 65 (05) :1637-1654
[9]   ASYMMETRIC MICHAEL ADDITIONS - REGIO-SELECTIVE, DIASTEREO-SELECTIVE, AND ENANTIOSELECTIVE ALKYLATIONS OF THE ENAMINES FROM BETA-TETRALONES AND (S)-2-(METHOXYMETHYL)PYRROLIDINE (PROLINOL METHYL-ETHER) BY OMEGA-NITROSTYRENES [J].
BLARER, SJ ;
SEEBACH, D .
CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (09) :3086-3096
[10]   ASYMMETRIC MICHAEL ADDITIONS CATALYZED BY NI(II) AND CO(II) COMPLEXES WITH HOMOCHIRAL LIGANDS [J].
BOTTEGHI, C ;
PAGANELLI, S ;
SCHIONATO, A ;
BOGA, C ;
FAVA, A .
JOURNAL OF MOLECULAR CATALYSIS, 1991, 66 (01) :7-21