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Enantio- and Diastereoselective Synthesis of Homoallylic ?-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.

ABSTRACT: We describe a strategy for the enantio- and diastereoselective synthesis of homoallylic ?-trifluoromethyl amines by the catalytic hydroalkylation of terminal dienes. Trifluoromethyl-substituted isatin-derived azadienolate nucleophiles undergo ?-selective alkylation with a Pd-DTBM-SEGPHOS catalyst, which additionally promotes regioselective addition to the diene and delivers products in up to 86% yield, 10:1 dr, and 97.5:2.5 er.

SUBMITTER: Onyeagusi CI

PROVIDER: S-EPMC7079280 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.

Onyeagusi Chibueze I CI Shao Xinxin X Malcolmson Steven J SJ

Organic letters 20200204 4

We describe a strategy for the enantio- and diastereoselective synthesis of homoallylic α-trifluoromethyl amines by the catalytic hydroalkylation of terminal dienes. Trifluoromethyl-substituted isatin-derived azadienolate nucleophiles undergo γ-selective alkylation with a Pd-DTBM-SEGPHOS catalyst, which additionally promotes regioselective addition to the diene and delivers products in up to 86% yield, 10:1 dr, and 97.5:2.5 er. ...[more]

PMID: 32013445

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