Issue 8, 2007

Highly stereoselective chlorination of β-substituted cyclic alcohols using PPh3–NCS: factors that control the stereoselectivity

Abstract

A variety of trans-β-substituted cyclic alcohols were stereoselectively chlorinated to either the corresponding cis-chloride or trans-chloride (inversion or retention of configuration) with good to excellent yields; the stereochemical outcome is determined by the size of the ring and the nature of the β-substituents, especially the electronegativity of the substituted atom.

Graphical abstract: Highly stereoselective chlorination of β-substituted cyclic alcohols using PPh3–NCS: factors that control the stereoselectivity

Supplementary files

Article information

Article type
Communication
Submitted
05 Oct 2006
Accepted
30 Oct 2006
First published
29 Nov 2006

Chem. Commun., 2007, 867-869

Highly stereoselective chlorination of β-substituted cyclic alcohols using PPh3NCS: factors that control the stereoselectivity

E. A. Jaseer, A. B. Naidu, S. S. Kumar, R. K. Rao, K. G. Thakur and G. Sekar, Chem. Commun., 2007, 867 DOI: 10.1039/B614512D

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