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Issue 17, 2020

Redox deracemization of diarylmethyl alkynes

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Abstract

Diarylmethyl alkynes with chirality at the propargylic position are privileged building blocks in many biologically important molecules. However, catalytic asymmetric access to such moieties has remained underdeveloped. Herein, we described a one-pot redox deracemization of diarylmethyl alkynes. By using MnO2 as a mild, inexpensive, and environmentally benign oxidant, combined with chiral phosphoric acid catalyzed asymmetric reduction, deracemization of diarylmethyl alkynes proceeds efficiently with high levels of chemo- and enantioselectivities. The generality of the strategy is further illustrated by redox deracemization of diarylmethyl alkenes.

Graphical abstract: Redox deracemization of diarylmethyl alkynes

Supplementary files

Article information


Submitted
07 Jul 2020
Accepted
04 Aug 2020
First published
05 Aug 2020

Org. Chem. Front., 2020,7, 2526-2530
Article type
Research Article

Redox deracemization of diarylmethyl alkynes

Y. Ma, X. Liu, Y. Mao, J. Huang, S. Ma and L. Liu, Org. Chem. Front., 2020, 7, 2526 DOI: 10.1039/D0QO00811G

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