Catalytic Asymmetric Mannich Reaction of α‑Fluoronitriles with Ketimines: Enantioselective and Diastereodivergent Construction of Vicinal Tetrasubstituted Stereocenters

Diastereodivergent and enantioselective conversion of isatin ketimines to α-fluoro-β-aminonitriles with vicinal tetrasubstituted stereocenters is achieved by a chiral copper complex/guanidine base-catalyzed Mannich reaction with proper choice of the bisphosphine ligand. The reaction is broad in scop...

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Bibliographic Details
Published in:ACS catalysis 2019-03, Vol.9 (3), p.2169-2176
Main Authors: Ding, Ransheng, De los Santos, Zeus A, Wolf, Christian
Format: Article
Language:English
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Summary:Diastereodivergent and enantioselective conversion of isatin ketimines to α-fluoro-β-aminonitriles with vicinal tetrasubstituted stereocenters is achieved by a chiral copper complex/guanidine base-catalyzed Mannich reaction with proper choice of the bisphosphine ligand. The reaction is broad in scope, scalable, and provides efficient access to a series of 3-aminoindolinones exhibiting a quaternary carbon–fluorine stereocenter with high yields and stereoselectivities. Selective transformations of the Mannich reaction products into multifunctional 3-aminooxindoles without erosion of enantiomeric and diastereomeric purity highlight the synthetic utility.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b05164