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Scientific article
English

Enantioselective halogenative semi-pinacol rearrangement: a stereodivergent reaction on a racemic mixture

Published inChemical communications, vol. 50, no. 88, p. 13461-13464
Publication date2014
Abstract

An efficient, quantitative deracemization strategy for optically inactive allylic cycloalkanols has been achieved using the biphasic halogenative semi-pinacol reaction protocol. The resultant β-halo spiroketones, containing three contiguous stereogenic centers, were easily recovered with high diastereomeric and enantiomeric purities following conventional silica gel chromatography. The optically active products could be further manipulated chemically, affording synthetically interesting scaffolds with complete preservation of stereoisomeric integrity.

Citation (ISO format)
ROMANOV MICHAILIDIS, Fedor et al. Enantioselective halogenative semi-pinacol rearrangement: a stereodivergent reaction on a racemic mixture. In: Chemical communications, 2014, vol. 50, n° 88, p. 13461–13464. doi: 10.1039/C4CC05923A
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ISSN of the journal1359-7345
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Creation10/09/2014 5:22:00 PM
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