Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 2, Pages 517-521Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo7018762
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[GRAPHICS] The unique reactivity of 2-methyleneoxetanes and 1,5-dioxaspiro[3.2]hexanes has been exploited for the synthesis of epi-oxetin (26), an oxetane-containing beta-amino acid. While the preparation of the natural product oxetin (1) was the original goal, the unexpected diastereoselectivity of an precedented reduction provided the epi-oxetin framework. The methodology described herein should be amenable for the preparation of oxetin with a change in nitrogen protection.
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