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Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes.

ABSTRACT: 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.

SUBMITTER: Yeung K

PROVIDER: S-EPMC5103189 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

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Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes.

Yeung Kay K Ruscoe Rebecca E RE Rae James J Pulis Alexander P AP Procter David J DJ

Angewandte Chemie (International ed. in English) 20160819 39

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. ...[more]

PMID: 27539673

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