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Wiley, Angewandte Chemie International Edition, 3(55), p. 1102-1107, 2015

DOI: 10.1002/anie.201508959

Wiley, Angewandte Chemie, 3(128), p. 1114-1119, 2015

DOI: 10.1002/ange.201508959

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Copper-Catalyzed Borylative Cross-Coupling of Allenes and Imines: Selective Three-Component Assembly of Branched Homoallyl Amines

Journal article published in 2015 by James Rae, Kay Yeung, Joseph J. W. McDouall ORCID, David J. Procter
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

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.