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Phosphine-Catalyzed Enantioselective Synthesis of Oxygen Heterocycles


  • We thank Prof. Qi-Lin Zhou, Kodak, and Degussa for generous gifts of catalysts and catalyst precursors. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, grant R01-GM57034), the Croucher Foundation (postdoctoral fellowship for Y.K.C.), Merck Research Laboratories, and Novartis.


Chiral phosphepine 1 catalyzes the transformation of an array of hydroxy-2-alkynoates into saturated oxygen heterocycles with good enantioselectivity. Phenols are also shown to participate in such phosphine-catalyzed cyclizations, including an asymmetric variant. This method provides a new approach to the enantioselective synthesis of tetrahydrofurans, tetrahydropyrans, and dihydrobenzopyrans.

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