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Enantioselective Bromolactonization Using an S-Alkyl Thiocarbamate Catalyst


  • We thank the National University of Singapore (Grant No. 143-000-509-112) for financial support. We acknowledge the receipt of both an NUS Research Scholarship (to X.J.) and a President’s Graduate Fellowship (to C.K.T.).


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The apple never falls far from the tree: S-alkyl thiocarbamate 1 (see scheme, NBP=N-bromophthalimide) was prepared in high yield through a synthetic sequence involving a Newman–Kwart rearrangement of the corresponding O-alkyl thiocarbamates. Compound 1 was used to catalyze bromolactonization, thus providing enantioenriched δ-lactones in excellent yield and enantioselectivity.