Redox-Neutral α-C–H Functionalization of Pyrrolidin-3-ol

作者：Cheng‐Bo Yi, Zhi-Ying She, Yong‐Feng Cheng, Jin Qu · 发表于：Organic Letters · 年份：2018 · DOI：10.1021/acs.orglett.7b03807 · 被引用次数：31 · 研究领域：Catalytic C–H Functionalization Methods、Oxidative Organic Chemistry Reactions、Asymmetric Synthesis and Catalysis

A redox-neutral α-C-H oxygenation of commercially available pyrrolidin-3-ol with a monoprotected p-quinone generated an N-aryliminium ion intermediate, which reacted in situ with boronic acid nucleophiles to produce a series of cis-2-substituted pyrrolidin-3-ols. With this strategy, 8-epi-(-)-lentiginosine was synthesized from (3R,4R)-pyrrolidine-3,4-diol in three steps.