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ChemRxiv Preprint Manuscript diene-isatin imine coupling.pdf (1.02 MB)
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Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes

preprint
submitted on 18.01.2020 and posted on 21.01.2020 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.

Funding

NIGMS R01 GM124286

NSF CHE-1800012

History

Email Address of Submitting Author

steven.malcolmson@duke.edu

Institution

Duke University

Country

United States of America

ORCID For Submitting Author

0000-0003-3229-0949

Declaration of Conflict of Interest

The authors declare no conflict of interest.

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