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Thia-Claisen rearrangements of S-allylic ketene N,S-acetals were carried out using substrates with an external allylic stereogenic centre. High levels of diastereoselectivity were observed only when a bromine substituent was introduced onto the double bond.

Diastereoselective Thia-Claisen Rearrangement of Pyrrolidinone-Derived [nl]Ketene N,S-Acetals