Lewis Acid-Mediated Highly Regioselective SN2-Type Ring-Opening of 2-Aryl-N-tosylazetidines and Aziridines by Alcohols

Lewis acid-mediated highly regioselective SN2-type ring-opening of 2-aryl-N-tosylazetidines with alcohols to afford various 1,3-amino ethers in excellent yields with good enantiomeric excess is described. Similar SN2-type ring-opening of chiral 2-phenyl-N-tosylaziridine with various alcohols produce...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-07, Vol.72 (15), p.5859-5862
Main Authors: Ghorai, Manas K, Das, Kalpataru, Shukla, Dipti
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Summary:Lewis acid-mediated highly regioselective SN2-type ring-opening of 2-aryl-N-tosylazetidines with alcohols to afford various 1,3-amino ethers in excellent yields with good enantiomeric excess is described. Similar SN2-type ring-opening of chiral 2-phenyl-N-tosylaziridine with various alcohols produces the corresponding nonracemic 1,2-amino ethers in excellent yields and good ee. The mechanism of the ring-opening of aziridines and azetidines via an SN2 pathway is supported by the formation of nonracemic amino ethers.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0703294