Tetrahedron letters

Regiochemistry of the thioenolates reaction with unsaturated ketones: C-versus S-1, 4-addition of a disbustituted dithioester thioenolate.

P Metzner, R Rakotonirina

Index: Metzner, Patrick; Rakotonirina, Rose Tetrahedron Letters, 1983 , vol. 24, # 39 p. 4203 - 4206

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Citation Number: 10

Abstract

Abstract Reaction of the lithium thioenolate of methyl 2-methyldithiopropanoate with enones gives kinetic sulphur 1, 4-addition or thermodynamic carbon 1, 4-addition, with the exception of cyclopent-2-enone which gives kinetic carbon 1, 4-addition. In all caess 5-oxodithioesters can be prepared in good yields. No 1, 2-addition is observed, confirming the soft nucleophilic character of dithioester thioenolates.