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

ABSTRACT: A copper-catalyzed three-component coupling of allenes, bis(pinacolato)diboron, and imines allows regio-, chemo-, and diastereoselective assembly of branched ?,?-substituted-?-boryl homoallylic amines, that is, products bearing versatile amino, alkenyl, and borane functionality. Alternatively, convenient oxidative workup allows access to ?-substituted-?-amino ketones. A computational study has been used to probe the stereochemical course of the cross-coupling.

SUBMITTER: Rae J

PROVIDER: S-EPMC4736445 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature

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

Rae James J Yeung Kay K McDouall Joseph J W JJ Procter David J DJ

Angewandte Chemie (International ed. in English) 20151203 3

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. ...[more]

PMID: 26632675

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