Kinetic resolution of 1, 2-diols with D-camphorquinone; preparation of (R)-(chloromethyl) oxirane

MK Ellis, BT Golding, WP Watson

Index: Ellis, Martin K.; Golding, Bernard T.; Watson, William P. Journal of the Chemical Society, Chemical Communications, 1984 , # 23 p. 1600 - 1602

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Citation Number: 8

Abstract

Acid-catalysed reaction of D-camphorquinone with racemic 1,2-diols (eg 3-chloropropane-I ,2-diol) under kinetically controlled conditions yields a predominant diastereoisomeric acetal, that can be easily converted into an optically pure epoxide. ... (R)- and (S)-(Chloromethy1)oxirane ['epichlorohydrins' (la) and (lb), respectively] are valuable starting materials for the preparation of optically active compounds. Both have been prepared by ...