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A General and Practical Synthesis of Chiral 1,2‐Oxazetidines

A General and Practical Synthesis of Chiral 1,2‐Oxazetidines 1,2‐Oxazetidines are valuable small strained molecules that could be used to create new and conventionally difficult‐to‐access chemical transformations. Currently, asymmetric methods towards this class of heterocycles are very rare. Herein, we report a general and practical method to access a series of structurally diverse chiral 1,2‐oxazetidines from readily available chiral epoxides and α‐bromo esters in 3–4 steps by using mild Mitsunobu reactions as an efficient ring‐closure approach to form the highly strained four‐membered rings. The new method is operationally simple, and a range of N‐nosyl‐protected 3‐ and 4‐substituted as well as 3,4‐disubstituted chiral 1,2‐oxazetidines could be conveniently prepared in gram‐scale with excellent enantioselectivities (93–99% ee) and good overall yields for the first time. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

A General and Practical Synthesis of Chiral 1,2‐Oxazetidines

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References (20)

Publisher
Wiley
Copyright
© 2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201900754
Publisher site
See Article on Publisher Site

Abstract

1,2‐Oxazetidines are valuable small strained molecules that could be used to create new and conventionally difficult‐to‐access chemical transformations. Currently, asymmetric methods towards this class of heterocycles are very rare. Herein, we report a general and practical method to access a series of structurally diverse chiral 1,2‐oxazetidines from readily available chiral epoxides and α‐bromo esters in 3–4 steps by using mild Mitsunobu reactions as an efficient ring‐closure approach to form the highly strained four‐membered rings. The new method is operationally simple, and a range of N‐nosyl‐protected 3‐ and 4‐substituted as well as 3,4‐disubstituted chiral 1,2‐oxazetidines could be conveniently prepared in gram‐scale with excellent enantioselectivities (93–99% ee) and good overall yields for the first time.

Journal

Asian Journal of Organic ChemistryWiley

Published: Feb 1, 2020

Keywords: ; ; ; ;

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