L-proline-catalyzed Michael addition of aldehydes and unmodified ketones to nitro olefins accelerated by Et3N

被引：18

作者：

Choudary, B. M.

Rajasekhar, Ch. V.

Krishna, G. Gopi

Reddy, K. Rajender

机构：

[1] Ogene Syst I Pvt Ltd, Hyderabad 500037, Andhra Pradesh, India

[2] Indian Inst Chem Technol, Inorgan & Phys Chem Div, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNTHETIC COMMUNICATIONS | 2007年 / 37卷 / 1-3期

关键词：

asymmetric synthesis; L-proline; Michael addition; nitroalkenes; organocatalysis; triethylamine;

D O I：

10.1080/00397910600978218

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved and efficient L-proline-catalyzed Michael addition of aldehydes and unmodified ketones with nitro olefins to afford delta-nitroketones in excellent yields and moderate enantioselectivities is described.

引用

页码：91 / 98

页数：8

共 25 条

[1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene
Alexakis, A
Andrey, O
[J]. ORGANIC LETTERS, 2002, 4 (21) : 3611 - 3614
[2] Organocatalytic Michael addition, a convenient tool in total synthesis. First asymmetric synthesis of (-)-botryodiplodin
Andrey, O
Vidonne, A
Alexakis, A
[J]. TETRAHEDRON LETTERS, 2003, 44 (43) : 7901 - 7904
[3] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine
Andrey, O
Alexakis, A
Bernardinelli, G
[J]. ORGANIC LETTERS, 2003, 5 (14) : 2559 - 2561
[4] BARNES J, 1999, J AM CHEM SOC, V126, P9558
[5] Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins
Betancort, JM
Sakthivel, K
Thayumanavan, R
Tanaka, F
Barbas, CF
[J]. SYNTHESIS-STUTTGART, 2004, (09): : 1509 - 1521
[6] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors
Betancort, JM
Barbas, CF
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3737 - 3740
[7] Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates
Betancort, JM
Sakthivel, K
Thayumanavan, R
Barbas, CF
[J]. 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
BLARER, SJ
SCHWEIZER, WB
SEEBACH, D
[J]. HELVETICA CHIMICA ACTA, 1982, 65 (05) : 1637 - 1654
[9] 5-Pyrrolidin-2-yltetrazole as an asymmetric organocatalyst for the addition of ketones to nitro-olefins
Cobb, AJA
Longbottom, DA
Shaw, DM
Ley, SV
[J]. CHEMICAL COMMUNICATIONS, 2004, (16) : 1808 - 1809
[10] In the golden age of organocatalysis
Dalko, PI
Moisan, L
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175

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