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

Adam Waldemar | Zendy; Zhang Aimin | Zendy

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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)

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