title: Enantioselective halogenative semi-pinacol rearrangement: a stereodivergent reaction on a racemic mixture.
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.
authors.affiliation: Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland. Alexandre.Alexakis@unige.ch.
authors.forename: Fedor
authors.initials: F
authors.lastname: Romanov-Michailidis
authors.forename: Marion
authors.initials: M
authors.lastname: Pupier
authors.forename: Laure
authors.initials: L
authors.lastname: Guénée
authors.forename: Alexandre
authors.initials: A
authors.lastname: Alexakis