Synthesis of Tetrahydropyran??4??ones and Thiopyran??4??ones from Donor??Substituted α??Bromostyrene Derivatives

A Rosiak, W Frey, J Christoffers

Index: Rosiak, Anna; Frey, Wolfgang; Christoffers, Jens European Journal of Organic Chemistry, 2006 , # 17 p. 4044 - 4054

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Citation Number: 25

Abstract

Abstract Tetrahydropyran-4-one and tetrahydrothiopyran-4-one derivatives with a 3-aryl substituent were synthesized by double-conjugate addition of water or H 2 S to divinyl ketones. These starting materials were prepared in two steps by conversion of lithiated α- bromostyrene derivatives with acrolein or cinnamaldehyde and subsequent oxidation of the divinyl alcohols with MnO 2. The electron-rich α-bromostyrene building blocks were ...