Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins

被引:192
作者
Betancort, JM
Sakthivel, K
Thayumanavan, R
Tanaka, F
Barbas, CF
机构
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[3] Scripps Res Inst, Dept Biol Mol, La Jolla, CA 92037 USA
来源
SYNTHESIS-STUTTGART | 2004年 / 09期
关键词
asymmetric catalysis; Michael additions; organocatalysis; ketones; enamines;
D O I
10.1055/s-2004-822392
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Michael additions of a number of ketones and aldehydes to alkylidene malonates and nitro olefins were studied. The reactions employ small organic molecules as catalyst under mild reaction conditions and do not require preactivation of the carbonyl donors. These reactions afforded a variety of highly functionalized products in good yields with moderate to good enantioselectivity.
引用
收藏
页码:1509 / 1521
页数:13
相关论文
共 92 条
[11]   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
[12]   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
[13]   ASYMMETRIC MICHAEL ADDITIONS - STEREOSELECTIVE ALKYLATIONS OF THE (R)-ENAMINE AND (S)-ENAMINE FROM CYCLOHEXANONE AND 2-(METHOXYMETHYL)PYRROLIDINE BY METHYL ALPHA-(METHOXYCARBONYL)CINNAMATES [J].
BLARER, SJ ;
SEEBACH, D .
CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (06) :2250-2260
[14]   Direct catalytic asymmetric aldol reactions of aldehydes [J].
Bogevig, A ;
Kumaragurubaran, N ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2002, (06) :620-621
[15]  
Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO
[16]  
2-Y
[17]   Direct and enantioselective organocatalytic α-chlorination of aldehydes [J].
Brochu, MP ;
Brown, SP ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4108-4109
[18]   The direct and enantioselective organocatalytic α-oxidation of aldehydes [J].
Brown, SP ;
Brochu, MP ;
Sinz, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10808-10809
[19]   A proline-catalyzed asymmetric Robinson annulation reaction [J].
Bui, T ;
Barbas, CF .
TETRAHEDRON LETTERS, 2000, 41 (36) :6951-6954
[20]  
Chowdari NS, 2003, SYNLETT, P1906