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High π‐Facial Selectivity Through Chelation of Magnesium Ions in the DMD Epoxidation of α,β‐Unsaturated Imides with Chiral Pyrrolidinone Auxiliaries
Author(s) -
Adam Waldemar,
Zhang Aimin
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300544
Subject(s) - chemistry , chelation , steric effects , hydroxymethyl , selectivity , magnesium , side chain , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , polymer
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)