Enantioselective Formal Hydration of α,β-Unsaturated Imides by Al-Catalyzed Conjugate Addition of Oxime Nucleophiles
- 26 October 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (45) , 14724-14725
- https://doi.org/10.1021/ja045563f
Abstract
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.Keywords
This publication has 5 references indexed in Scilit:
- Highly Stereoselective Intermolecular Oxy-Michael Addition Reaction to α,β-Unsaturated Malonate EstersOrganic Letters, 2004
- Concise Synthesis of Anti-HIV-1 Active (+)-Inophyllum B and (+)-Calanolide A by Application of (−)-Quinine-Catalyzed Intramolecular Oxo-Michael AdditionThe Journal of Organic Chemistry, 2004
- Difluorphos, an Electron‐Poor Diphosphane: A Good Match Between Electronic and Steric FeaturesAngewandte Chemie International Edition in English, 2003
- Highly Diastereoselective Oxy‐Michael Additions of Enantiopure δ‐Lactol Anions to Nitroalkenes: Asymmetric Synthesis of 1,2‐Amino AlcoholsAngewandte Chemie International Edition in English, 2003
- Highly Enantioselective, Catalytic Conjugate Addition of Cyanide to α,β-Unsaturated ImidesJournal of the American Chemical Society, 2003