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ChemRxiv Preprint Manuscript diene-isatin imine coupling.pdf (1.02 MB)

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

submitted on 18.01.2020, 22:11 and posted on 21.01.2020, 09:32 by Chibueze I. Onyeagusi, Xinxin Shao, Steven Malcolmson
We describe a strategy for the enantio- and diastereoselective synthesis of homoallylic α-trifluoromethyl amines by the catalytic hydroalkylation of terminal dienes. Trifluoromethylsubstituted 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.


NIGMS R01 GM124286

NSF CHE-1800012


Email Address of Submitting Author


Duke University


United States of America

ORCID For Submitting Author


Declaration of Conflict of Interest

The authors declare no conflict of interest.