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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.
Asian Journal of Organic Chemistry – Wiley
Published: Feb 1, 2020
Keywords: ; ; ; ;
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