Organocatalytic asymmetric "anti-Michael" reaction of β-ketoesters

被引：37

作者：

Aleman, Jose ^{[1
]}

Reyes, Efraim ^{[1
]}

Richter, Bo ^{[1
]}

Overgaard, Jacob ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Ctr Catal, Danish Natl Res Fdn, Dept Chem, DK-8000 Aarhus, Denmark

来源：

CHEMICAL COMMUNICATIONS | 2007年 / 38期

关键词：

D O I：

10.1039/b710393j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first organocatalytic "anti-Michael'' reaction of cyclic-beta-ketoesters to unsaturated double bonds is described in a highly asymmetric version leading to the synthesis of alpha,alpha'-di-substituted branched double bonds as optically active Baylis-Hillman-like adducts.

引用

页码：3921 / 3923

页数：3

共 49 条

[31]

O'Donnell M. J., 2000, CATALYTIC ASYMMETRIC, P727

[32] Enantio- and diastereoselective catalytic Mannich-type reaction of a glycine Schiff base using a chiral two-center phase-transfer catalyst [J].

Okada, A ;

Shibuguchi, T ;

Ohshima, T ;

Masu, H ;

Yamaguchi, K ;

Shibasaki, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (29) :4564-4567

[33] Asymmetric Strecker reaction of aldimines using aqueous potassium cyanide by phase-transfer catalysis of chiral quaternary ammonium salts with a tetranaphthyl backbone [J].

Ooi, T ;

Uematsu, Y ;

Maruoka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2548-2549

[34] Design of N-spiro C2-symmetric chiral quaternary ammonium bromides as novel chiral phase-transfer catalysts:: Synthesis and application to practical asymmetric synthesis of α-amino acids [J].

Ooi, T ;

Kameda, M ;

Maruoka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (17) :5139-5151

[35]

OOI T, 2003, ANGEW CHEM INT EDIT, V42, P3981

[36] Recent advances in asymmetric phase-transfer catalysis [J].

Ooi, Takashi ;

Maruoka, Keiji .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (23) :4222-4266

[37]

Park HG, 2002, ANGEW CHEM INT EDIT, V41, P3036, DOI 10.1002/1521-3773(20020816)41:16<3036::AID-ANIE3036>3.0.CO

[38]

2-3

[39]

Perlmutter P., 1992, CONJUGATE ADDITION R

[40] Organocatalytic asymmetric direct α-alkynylation of cyclic β-ketoesters [J].

Poulsen, Thomas B. ;

Bernardi, Luca ;

Aleman, Jose ;

Overgaard, Jacob ;

Jorgensen, Karl Anker .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (02) :441-449

← 1 2 3 4 5 →