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Chem Commun (Camb). 2019 Jan 24;55(9):1263-1266. doi: 10.1039/c8cc07949h.

Enantioenrichment of racemic BINOL by way of excited state proton transfer.

Author information

1
Department of Chemistry & Biochemistry, Florida State University, Tallahassee, Florida 32306, USA. hanson@chem.fsu.edu.

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.

PMID:
30632552
DOI:
10.1039/c8cc07949h

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