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Redox-Neutral α-C-H Functionalization of Pyrrolidin-3-ol
Cheng-Bo Yi1, Zhi-Ying She1, Yong-Feng Cheng1
1The State Key Laboratory and Institute of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University , Tianjin 300071, China.
Abstract:
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.
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