Tetrahedron

Diastereoselectivity of the thio-Claisen rearrangement of acyclic precursors bearing a chiral centre adjacent to carbon 6

S Désert, P Metzner

Index: Desert, Stephane; Metzner, Patrick Tetrahedron, 1992 , vol. 48, # 47 p. 10327 - 10338

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Citation Number: 16

Abstract

A number of chiral allylic alcohols have been prepared and submitted to a Mitsunobu reaction with dithioacetic acid. Allyl dithioesters were deprotonated by LDA at− 30° C and resulting enethiolates were quenched with iodomethane to afford quantitatively S-allyl ketenedithioacetals. These precursors undergo a thio-Claisen rearrangement under smooth conditions: room temperature or heating at 101° C. The diastereoselectivity of this ...