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

Chibueze I. Onyeagusi | Zendy; Xinxin Shao | Zendy; Steven J. Malcolmson | Zendy

Open Access

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

Author(s) -

Chibueze I. Onyeagusi,

Xinxin Shao,

Steven J. Malcolmson

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c00342

Subject(s) - chemistry , trifluoromethyl , catalysis , organic chemistry , combinatorial chemistry , alkyl

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.

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