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Enantioselective Generation of Adjacent Stereocenters in a Copper‐Catalyzed Three‐Component Coupling of Imines, Allenes, and Diboranes
Author(s) -
Yeung Kay,
Ruscoe Rebecca E.,
Rae James,
Pulis Alexander P.,
Procter David J.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201606710
Subject(s) - stereocenter , enantioselective synthesis , copper , catalysis , component (thermodynamics) , chemistry , ligand (biochemistry) , coupling (piping) , combinatorial chemistry , organic chemistry , materials science , physics , biochemistry , receptor , metallurgy , thermodynamics
A highly enantio‐ and diastereoselective copper‐catalyzed three‐component coupling affords the first general synthesis of homoallylic amines bearing adjacent stereocenters from achiral starting materials. The method utilizes a commercially available NHC ligand and copper source, operates at ambient temperature, couples readily available simple imines, allenes, and diboranes, and yields high‐value homoallylic amines that exhibit versatile amino, alkenyl, and boryl units.