Blauvelt Marisa L, Howell Amy R
Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, USA.
J Org Chem. 2008 Jan 18;73(2):517-21. doi: 10.1021/jo7018762. Epub 2007 Dec 20.
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.
2-亚甲基氧杂环丁烷和1,5-二氧杂螺[3.2]己烷的独特反应活性已被用于合成表氧杂环丁烷（26），一种含氧杂环丁烷的β-氨基酸。虽然制备天然产物氧杂环丁烷（1）是最初的目标，但一个前所未有的还原反应意外的非对映选择性提供了表氧杂环丁烷骨架。本文所述方法经氮保护的改变后应适用于氧杂环丁烷的制备。
