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Issue 9, 2019
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Enantioenrichment of racemic BINOL by way of excited state proton transfer

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Abstract

Here we report a method for enantioenriching BINOL using a chiral auxiliary and an excited state proton transfer (ESPT) event. Regardless of the starting enantiomeric excess (ee), after irradiation the solution reaches a photostationary state whose ee is dependent solely on the identity of the chiral auxiliary group. The enantioenriched BINOL is easily recovered by cleaving the auxiliary group in mild conditions.

Graphical abstract: Enantioenrichment of racemic BINOL by way of excited state proton transfer

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Article information


Submitted
04 Oct 2018
Accepted
02 Jan 2019
First published
02 Jan 2019

Chem. Commun., 2019,55, 1263-1266
Article type
Communication

Enantioenrichment of racemic BINOL by way of excited state proton transfer

S. Ayad, V. Posey, A. Das, J. M. Montgomery and K. Hanson, Chem. Commun., 2019, 55, 1263
DOI: 10.1039/C8CC07949H

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