Tetrahedron

Reaction of epoxides with activated DMSO reagent. General method for synthesis of α-chlorocarbonyl compounds: Application in asymmetric synthesis of (3S)-2, 3- …

S Raina, VK Singh

Index: Raina, Sushil; Singh, Vinod K. Tetrahedron, 1995 , vol. 51, # 8 p. 2467 - 2476

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Citation Number: 21

Abstract

Reaction of a variety of epoxides with DMSO-Oxalyl chloride in the presence of a catalytic amount of methanol and a base was studied. Disubstituted epoxides gave α-chloroketones in high yields. Aliphatic terminal epoxide underwent opening reaction to provide α- chloroketone as a major product. Trisubstututed epoxides provided α-chloroketones as major products through the formation of more stable carbocation. In case of a homoallylic ...