Diastereoselective Epoxidation of Oxazolidine-Substituted Alkenes by Dimethyldioxirane and m-Chloroperbenzoic Acid:  π-Facial Control through Hydrogen Bonding by the Urea Functionality

A high diastereoselectivity (up to >98:2) is found for the DMD and m-CPBA epoxidations of chiral oxazolidine-substituted olefins with a urea group. The selectivity is explained in terms of hydrogen bonding between the remote NH group of the urea functionality and the epoxidizing reagent. Methylat...

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Bibliographic Details
Published in:Organic letters 2001-01, Vol.3 (1), p.79-82
Main Authors: Adam, Waldemar, Schambony, Simon B
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Amines - chemistry
Catalysis
Chlorobenzoates - chemistry
Epoxy Compounds
Hydrogen Bonding
Magnetic Resonance Spectroscopy
Methylation
Molecular Structure
Oxazoles
Stereoisomerism
Structure-Activity Relationship
Urea - chemistry
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Summary:A high diastereoselectivity (up to >98:2) is found for the DMD and m-CPBA epoxidations of chiral oxazolidine-substituted olefins with a urea group. The selectivity is explained in terms of hydrogen bonding between the remote NH group of the urea functionality and the epoxidizing reagent. Methylation of the NH group prohibits hydrogen bonding, and a reversed selectivity is observed due to steric repulsion between the reagent and the urea functionality.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol006800w