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Issue 17, 2020
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Redox deracemization of diarylmethyl alkynes

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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

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Article information

07 Jul 2020
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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