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Title

Enantioselective halogenative semi-pinacol rearrangement: a stereodivergent reaction on a racemic mixture
Authors
Romanov Michailidis, Fedor
Pupier, Marion
Guenee, Laure
Alexakis, Alexandre
Published in Chemical Communications. 2014, vol. 50, no. 88, p. 13461-13464
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.
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Article (Published version) (1.4 MB) - document accessible for UNIGE members only Limited access to UNIGE
Other version: http://xlink.rsc.org/?DOI=C4CC05923A
Structures
Faculté des sciences / Section de chimie et biochimie / Département de chimie minérale, analytique et appliquée
Faculté des sciences / Section de chimie et biochimie / Département de chimie organique
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. https://archive-ouverte.unige.ch/unige:40861

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Deposited on : 2014-10-13

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