Catalytic Asymmetric Intermolecular Stetter Reaction of Glyoxamides with Alkylidenemalonates

被引：219

作者：

Liu, Qin ^{[1
]}

Perreault, Stephane ^{[1
]}

Rovis, Tomislav ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 43期

关键词：

D O I：

10.1021/ja805680z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An asymmetric intermolecular Stetter reaction of glyoxamide and alkylidenemalonates has been developed. Catalyzed by a novel N-heterocyclic carbene, the Stetter adducts are formed in good yield and excellent enantioselectivity. The presence of a sensitive epimerizable stereocenter is tolerated under these mildly basic reaction conditions if a bulky amine base is used. The products may be further elaborated to provide synthetically useful intermediates.

引用

页码：14066 / +

页数：3

共 31 条

[1] New developments in the asymmetric Stetter reaction [J].

Christmann, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (18) :2632-2634

[2] Scope of the asymmetric intramolecular Stetter reaction catalyzed by chiral nucleophilic triazolinylidene carbenes [J].

de Alaniz, Javier Read ;

Kerr, Mark S. ;

Moore, Jennifer L. ;

Rovis, Tornislav .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (06) :2033-2040

[3] A highly enantio- and diastereoselective catalytic intramolecular stetter reaction [J].

de Alaniz, JR ;

Rovis, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) :6284-6289

[4] Nucleophilic carbenes in asymmetric organocatalysis [J].

Enders, D ;

Balensiefer, T .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :534-541

[5] The first asymmetric intramolecular Stetter reaction [J].

Enders, D ;

Breuer, K ;

Runsink, J ;

Teles, JH .

HELVETICA CHIMICA ACTA, 1996, 79 (07) :1899-1902

[6]

Enders D., 1999, COMPREHENSIVE ASYMME, P1093

[7] Asymmetric intermolecular Stetter reactions catalyzed by a novel triazolium derived N-heterocyclic carbene [J].

Enders, Dieter ;

Han, Jianwei ;

Henseler, Alexander .

CHEMICAL COMMUNICATIONS, 2008, (34) :3989-3991

[8] Organocatalysis by N-heterocyclic, carbenes [J].

Enders, Dieter ;

Niemeier, Oliver ;

Henseler, Alexander .

CHEMICAL REVIEWS, 2007, 107 (12) :5606-5655

[9] Organocatalytic asymmetric conjugate nucleophilic glyoxylation [J].

Enders, Dieter ;

Bonten, Maurice Hubert ;

Raabe, Gerhard .

SYNLETT, 2007, (06) :885-888

[10] Asymmetric nucleophilic glyoxylation through a metalated α-aminonitrile derivative in Michael additions to nitroalkenes [J].

Enders, Dieter ;

Bonten, Maurice Hubert ;

Raabe, Gerhard .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (13) :2314-2316

← 1 2 3 4 →