New developments in the asymmetric Stetter reaction

被引：229

作者：

Christmann, M ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 18期

关键词：

asymmetric catalysis; carbenes; organocatalysis; Stetter reaction; umpolung;

D O I：

10.1002/anie.200500761

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Highly active carbene catalysts have revitalized the interest in the asymmetric Stetter reaction as a method for the construction of 1,4-dicarbonyl compounds. With the latest generation of a catalyst developed by Rovis and co-workers (1, for example), products with quaternary stereocenters such as 2 can be generated in 85% yield and 99% ee. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2632 / 2634

页数：3

共 33 条

[1] Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot Sila-Stetter/Paal-Knorr strategy
Bharadwaj, AR
Scheidt, KA
[J]. ORGANIC LETTERS, 2004, 6 (14) : 2465 - 2468
[2] A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-knorr sequence
Braun, RU
Zeitler, K
Muller, TJJ
[J]. ORGANIC LETTERS, 2001, 3 (21) : 3297 - 3300
[3] ON THE MECHANISM OF THIAMINE ACTION .4. EVIDENCE FROM STUDIES ON MODEL SYSTEMS
BRESLOW, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) : 3719 - 3726
[4] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones
Burstein, C
Glorius, F
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) : 6205 - 6208
[5] Burstein C., 2004, ANGEW CHEM, V116, P6331
[6] Nucleophilic carbenes in asymmetric organocatalysis
Enders, D
Balensiefer, T
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 534 - 541
[7] Enders D, 2002, ANGEW CHEM INT EDIT, V41, P1743, DOI 10.1002/1521-3773(20020517)41:10<1743::AID-ANIE1743>3.0.CO
[8] 2-Q
[9] The first asymmetric intramolecular Stetter reaction
Enders, D
Breuer, K
Runsink, J
Teles, JH
[J]. HELVETICA CHIMICA ACTA, 1996, 79 (07) : 1899 - 1902
[10] Enders D., 2002, ANGEW CHEM, V114, P1822

← 1 2 3 4 →