Simple diamine- and triamine-protonic acid catalysts for the enantioselective Michael addition of cyclic ketones to nitroalkenes

被引：199

作者：

Pansare, Sunil V. ^{[1
]}

Pandya, Keyur ^{[1
]}

机构：

[1] Mem Univ Newfoundland, Dept Chem, St John, NF A1B 3X7, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 30期

关键词：

D O I：

10.1021/ja062701n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Simple, chiral, pyrrolidine-based diamine and triamine derivatives that incorporate the secondary-secondary diamine motif are efficient catalysts for the highly diastereoselective and enantioselective Michael addition of cyclic ketones to 2-nitrovinyl arenes. The highest selectivities are obtained when these catalysts are used in conjunction with protonic acids. Steric factors in the substrate and the size of the acid additive play an important role in stereoselection. Copyright © 2006 American Chemical Society.

引用

页码：9624 / 9625

页数：2

共 21 条

[1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].

Alexakis, A ;

Andrey, O .

ORGANIC LETTERS, 2002, 4 (21) :3611-3614

[2] The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins [J].

Andrey, O ;

Alexakis, A ;

Tomassini, A ;

Bernardinelli, G .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1147-1168

[3] 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

[4] 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

[5] Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions [J].

Cobb, AJA ;

Shaw, DM ;

Longbottom, DA ;

Gold, JB ;

Ley, SV .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) :84-96

[6] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[7] Highly enantioselective organocatalytic conjugate addition of malonates to acyclic α,β-unsaturated enones [J].

Halland, N ;

Aburel, PS ;

Jorgensen, KA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (06) :661-665

[8] Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst [J].

Huang, Hongbing ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) :7170-7171

[9] 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

[10] Asymmetric organocatalytic conjugate addition of malonates to enones using a proline tetrazole catalyst [J].

Knudsen, KR ;

Mitchell, CET ;

Ley, SV .

CHEMICAL COMMUNICATIONS, 2006, (01) :66-68

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