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Copper‐Catalyzed Borylative Cross‐Coupling of Allenes and Imines: Selective Three‐Component Assembly of Branched Homoallyl Amines
Author(s) -
Rae James,
Yeung Kay,
McDouall Joseph J. W.,
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.201508959
Subject(s) - chemistry , borane , component (thermodynamics) , catalysis , copper , coupling (piping) , allene , combinatorial chemistry , oxidative coupling of methane , amine gas treating , organic chemistry , materials science , physics , metallurgy , thermodynamics
A copper‐catalyzed three‐component coupling of allenes, bis(pinacolato)diboron, and imines allows regio‐, chemo‐, and diastereoselective assembly of branched α,β‐substituted‐γ‐boryl homoallylic amines, that is, products bearing versatile amino, alkenyl, and borane functionality. Alternatively, convenient oxidative workup allows access to α‐substituted‐β‐amino ketones. A computational study has been used to probe the stereochemical course of the cross‐coupling.