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Enantioselective, Desymmetrizing Bromolactonization of Alkynes

2013; American Chemical Society; Volume: 135; Issue: 22 Linguagem: Inglês

10.1021/ja402910d

1943-2984

Michael Wilking, Christian Mück‐Lichtenfeld, Constantin G. Daniliuc, Ulrich Hennecke,

Asymmetric Synthesis and Catalysis

Asymmetric bromolactonizations of alkynes are possible using a desymmetrization approach. The commercially available catalyst (DHQD)2PHAL promotes these cyclizations in combination with cheap NBS as a bromine source to give bromoenol lactones in high yield and with high enantioselectivity. The bromoenol lactone products, containing a tetrasubstituted alkene and a quaternary stereocenter, are valuable building blocks for synthetic chemistry.