Diastereocontrol of thio-Claisen rearrangement induced by an adjacent hydroxy-substituted chiral centre

Abstract
S-Allyl α-hydroxy ketene dithioacetals smoothly rearrange into α-allyl β-hydroxydithioesters with a high level of syn-diastereoselectivity, with the syn : anti ratio ranging from 24:1 to 6:1, independently of the geometry of the ketene double bond.

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