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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Regio- and Enantioselective Functionalization of Quinone Imine Ketals Enabled by Gold and CPA Relay Catalysis
Xiaolan Xin1, Xudong Wang1, Zi-Qiang Rong1
1State Key Laboratory of Flexible Electronics (LoFE) and Institute of Flexible Electronics (IFE), Northwestern Polytechnical University (NPU) 127 West Youyi Road, Xi'an 710072, China.
Abstract:
A relay catalytic system that combines AuCl with a chiral phosphoric acid enables asymmetric annulation of racemic α-amino ynones with quinone imine ketals, furnishing fully substituted pyrrol-3(2H)-ones bearing quaternary stereocenters. The reaction shows high regio- and enantioselectivity, broad tolerance of α-amino ynones, and compatibility with selected QIK variants, affording products in up to 93% yield and 98% ee. Millimole-scale synthesis and transformations demonstrate its synthetic utility.
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