Synthesis of γ-Lactams by Mild, o-Benzoquinone-Induced Oxidation of Pyrrolidines Containing Oxidation-Sensitive Functional Groups

作者：Hao‐Jie Rong, Yong‐Feng Cheng, Fan-Fan Liu, Shu‐Jian Ren, Jin Qu · 发表于：The Journal of Organic Chemistry · 年份：2016 · DOI：10.1021/acs.joc.6b02562 · 被引用次数：33 · 研究领域：Oxidative Organic Chemistry Reactions、Asymmetric Synthesis and Catalysis、Synthesis and Catalytic Reactions

The late-stage oxidation of substituted pyrrolidines offers good flexibility for the construction of γ-lactam libraries, and especially in recent years the methods for functionalization of pyrrolidine have been available. We reported a new strategy for oxidation of pyrrolidines to γ-lactams: reaction of pyrrolidine with an o-benzoquinone gives an N,O-acetal by direct oxidation of the α-C-H bond of the pyrrolidine ring, and then the N,O-acetal is further oxidized by the o-benzoquinone to the γ-lactam. Because the first oxidation occurs selectively at the α-C-H of the pyrrolidine ring, oxidation-sensitive functional groups (allyl-, vinyl-, hydroxyl-, and amino groups) on pyrrolidine ring are unaffected. The synthetic utility of this novel method was demonstrated by the facile syntheses of (S)-vigabatrin and two analogues.