Stereoselective Synthesis of Vinylcyclopropa[<i>b</i>]indolines via a Rh-Migration Strategy
Pan Guo, Wangbin Sun, Yu Liu, Yongxin Li, Teck‐Peng Loh, Yaojia Jiang
Abstract
A mild rhodium catalytic system has been developed to synthesize vinylcyclopropa[b]indolines through cyclopropanation of indoles with vinyl carbenoids generated from ring opening of cyclopropenes in situ. By employing a Rh-migration strategy, the products can be obtained with good to excellent E:Z ratios (≤99:1) and complete diastereoselectivity (≤99:1). This method is easy, has a low catalyst loading, and works for a broad range of functionalities.
Topics & Concepts
CyclopropanationRhodiumChemistryStereoselectivityCatalysisIn situCombinatorial chemistryRing (chemistry)StereochemistryOrganic chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions