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Intermolecular Hydroamination of 1,3-Dienes To Generate Homoallylic Amines.

ABSTRACT: We report a Rh-catalyzed hydroamination of 1,3-dienes to generate homoallylic amines. Our work showcases the first case of anti-Markovnikov selectivity in the intermolecular coupling of amines and 1,3-dienes. By tuning the ligand properties and Brønsted acid additive, we find that a combination of rac-BINAP and mandelic acid is critical for achieving anti-Markovnikov selectivity.

SUBMITTER: Yang XH

PROVIDER: S-EPMC6563820 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Intermolecular Hydroamination of 1,3-Dienes To Generate Homoallylic Amines.

Yang Xiao-Hui XH Lu Alexander A Dong Vy M VM

Journal of the American Chemical Society 20170927 40

We report a Rh-catalyzed hydroamination of 1,3-dienes to generate homoallylic amines. Our work showcases the first case of anti-Markovnikov selectivity in the intermolecular coupling of amines and 1,3-dienes. By tuning the ligand properties and Brønsted acid additive, we find that a combination of rac-BINAP and mandelic acid is critical for achieving anti-Markovnikov selectivity. ...[more]

PMID: 28953374

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