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Enantioselective Coupling of Nitroesters and Alkynes

preprint
submitted on 19.10.2020, 00:05 and posted on 19.10.2020, 13:06 by Ryan Davison, Patrick Parker, Xintong Hou, Crystal Chung, Sara Augustine, Vy M. Dong

By using Rh-H catalysis, we couple α-nitroesters and alkynes to prepare α-amino acid surrogates. This atom-economical strategy generates two contiguous stereocenters, with high enantio- and diastereocontrol. In this transformation, the alkyne undergoes isomerization to generate a Rh(III)-π-allyl electrophile, which is trapped by an α-nitroester nucleophile. A subsequent reduction with In powder transforms the allylic α-nitroesters to the corresponding α,α- disubstituted α-amino esters.

Funding

National Institutes of Health (R35GM127071)

University of California, Irvine

History

Email Address of Submitting Author

dongv@uci.edu

Institution

University of California, Irvine

Country

United States

ORCID For Submitting Author

0000-0002-8099-1048

Declaration of Conflict of Interest

The authors declare no competing financial interests.

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