Organic process research & development

Enantioselective synthesis of hydrobenzofuranones using an asymmetric desymmetrizing intramolecular Stetter reaction of cyclohexadienones

Q Liu, T Rovis

Index: Liu, Qin; Rovis, Tomislav Organic Process Research and Development, 2007 , vol. 11, # 3 p. 598 - 604

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Citation Number: 44

Abstract

A series of cyclohexadienones were synthesized by dearomatization of phenols followed by Dess-Martin oxidation. Asymmetric intramolecular Stetter reactions of these substrates provide hydrobenzofuranones in good to excellent yields and excellent stereoselectivities. Up to three stereocenters as well as a quaternary stereocenter are formed from polysubstituted substrates. A scale-up experiment demonstrates the utility of this ...