Enantioselective alkylation of acyclic α,α-disubstituted tributyltin enolates catalyzed by a {Cr(salen)) complex

被引：88

作者：

Doyle, Abigail G. ^{[1
]}

Jacobsen, Eric N. ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 20期

关键词：

alkylation; asymmetric catalysis; chromium; enolates; N; O ligands;

D O I：

10.1002/anie.200604901

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Straighten out the mixture: A dynamic mixture of acyclic isomers of tributyltin enolates undergoes a {Cr(salen)}-catalyzed alkylation reaction to generate methyl ketones that contain α-carbonyl quaternary stereocenters in high yield and enantioselectivity (salen = N,N′-bis(salicylidene) ethylenediamine dianion). A mechanism is proposed which involves halide activation by a cationic metal complex. (Chemical Equation Presented). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3701 / 3705

页数：5

共 65 条

[1] Stereoselective construction of a quaternary carbon substituted with multifunctional groups: application to the concise synthesis of (+)-ethosuximide [J].

Abe, T ;

Suzuki, T ;

Sekiguchi, K ;

Hosokawa, S ;

Kobayashi, S .

TETRAHEDRON LETTERS, 2003, 44 (52) :9303-9305

[2] Asymmetric arylation of ketone enolates [J].

Ahman, J ;

Wolfe, JP ;

Troutman, MV ;

Palucki, M ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1918-1919

[3]

[Anonymous], 1999, COMPREHENSIVE ASYMME

[4]

[Anonymous], 2006, ANGEW CHEM

[5]

[Anonymous], 2003, ANGEW CHEM

[6] A practical chiral bicyclic thioglycolate lactam auxiliary for stereoselective quaternary carbon formation [J].

Arpin, A ;

Manthorpe, JM ;

Gleason, JL .

ORGANIC LETTERS, 2006, 8 (07) :1359-1362

[7] The enantioselective Tsuji allylation [J].

Behenna, DC ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045

[8] Organocatalytic enantioselective conjugate addition to alkynones [J].

Bella, M ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) :5672-5673

[9] THE REACTION BETWEEN AROMATIC COMPOUNDS AND DERIVATIVES OF TERTIARY ACIDS .11. FRIEDEL-CRAFTS REACTIONS WITH OPTICALLY ACTIVE ACID CHLORIDES [J].

BLEAZARD, W ;

ROTHSTEIN, E .

JOURNAL OF THE CHEMICAL SOCIETY, 1958, (NOV) :3789-3794

[10] Toward the development of a general chiral auxiliary. 9. Highly diastereoselective alkylations and acylations to form tertiary and quaternary centers [J].

Boeckman, RK ;

Boehmler, DJ ;

Musselman, RA .

ORGANIC LETTERS, 2001, 3 (23) :3777-3780

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