High π-Facial Selectivity Through Chelation of Magnesium Ions in the DMD Epoxidation of α,β-Unsaturated Imides with Chiral Pyrrolidinone Auxiliaries

✍ Scribed by Waldemar Adam; Aimin Zhang

• Book ID: 102170968
• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 143 KB
• Volume: 2004
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200300544

✦ Synopsis

Abstract

High diastereoselectivity, but of the opposite sense, is observed in the epoxidation (DMD or __m__CPBA) of α,β‐unsaturated imides equipped with pyrrolidinone‐type chiral auxiliaries that bear either a hydroxymethyl or trityloxymethyl side chain. This unprecedented reversed π‐facial differentiation is promoted by chelation of a magnesium ion, which results in conformational control over the essential steric interactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)