Enantioselective formal hydration of α,β-unsaturated imides by Al-catalyzed conjugate addition of oxime nucleophiles

被引：139

作者：

Vanderwal, CD ^{[1
]}

Jacobsen, EN ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 45期

关键词：

D O I：

10.1021/ja045563f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The (salen)Al-catalyzed asymmetric conjugate addition of salicylaldoxime to α,β-unsaturated imides is the key step in an efficient and highly enantioselective two-step formal hydration of these electron-deficient olefins. This reaction constitutes the first example of an enantioselective conjugate addition of an oxygen-centered nucleophile to α,β-unsaturated carboxylic acid derivatives. Application of this method to chiral, nonracemic substrates revealed a high level of catalyst-induced diastereoselectivity, underscoring its potential utility for polyketide natural product synthesis. Copyright © 2004 American Chemical Society.

引用

页码：14724 / 14725

页数：2

共 50 条

[11] Enantioselective conjugate addition of hydrazines to α,β- unsaturated imides. Synthesis of chiral pyrazolidinones
Sibi, Mukund P.
Soeta, Takahiro
Journal of the American Chemical Society, 2007, 129 (15): : 4522 - 4523
[12] Organocatalytic Enantioselective Formal Conjugate Addition of a Hydroxymoyl Anion to α,β-Unsaturated Aldehydes
Alonso, Beatriz
Reyes, Efraim
Carrillo, Luisa
Vicario, Jose L.
Badia, Dolores
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (22) : 6048 - 6051
[13] Highly enantioselective catalytic conjugate addition of N-heterocycles to α,β-unsaturated ketones and imides
Gandelman, M
Jacobsen, EN
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) : 2393 - 2397
[14] Enantioselective Copper-Catalyzed Conjugate Addition of Trimethylaluminium to β,γ-Unsaturated α-Ketoesters
Gremaud, Ludovic
Alexakis, Alexandre
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (03) : 794 - 797
[15] Enantioselective Michael additions to α,β-unsaturated imides catalyzed by a Salen-Al complex
Taylor, MS
Jacobsen, EN
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) : 11204 - 11205
[16] Enantioselective organocatalytic conjugate addition of organoboron nucleophiles
Nguyen, Truong N.
May, Jeremy A.
TETRAHEDRON LETTERS, 2017, 58 (16) : 1535 - 1544
[17] Copper-catalyzed regio- and enantioselective formal conjugate addition of Grignard reagents to a,b-unsaturated aldehydes
Mastral, Martin Fananas
Feringa, Ben L.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[18] Ir-Catalyzed Enantioselective Formal C-H Conjugate Addition of Pyrrole and Indoles to α,β-Unsaturated Carbonyl Compounds
Shibata, Takanori
Sasaki, Mio
Kojima, Masafumi
Ito, Mamoru
ORGANIC LETTERS, 2021, 23 (23) : 9078 - 9082
[19] Rhodium-catalyzed enantioselective conjugate addition of organoboronic acids to α,β-unsaturated sulfones
Mauleón, P
Carretero, JC
ORGANIC LETTERS, 2004, 6 (18) : 3195 - 3198
[20] Copper-catalyzed enantioselective conjugate addition of Grignard reagents to α,β-unsaturated esters
López, F
Harutyunyan, SR
Meetsma, A
Minnaard, AJ
Feringa, BL
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (18) : 2752 - 2756

← 1 2 3 4 5 →