Journal article
Enantioselective halogenative semi-pinacol rearrangement: a stereodivergent reaction on a racemic mixture.
- Romanov-Michailidis F Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland. Alexandre.Alexakis@unige.ch.
- Pupier M
- Guénée L
- Alexakis A
- 2014-09-20
Published in:
- Chemical communications (Cambridge, England). - 2014
English
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.
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1039/c4cc05923a
- PMID 25234590
- Persistent URL
- https://sonar.ch/global/documents/221642
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