Carbanion-accelerated Claisen rearrangements. 6. Preparative and stereochemical studies with sulfonyl-stabilized anions

SE Denmark, MA Harmata…

Index: Denmark, Scott E.; Harmata, Michael A.; White, Kathleen S. Journal of the American Chemical Society, 1989 , vol. 111, # 24 p. 8878 - 8891

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Citation Number: 23

Abstract

Abstract: The aliphatic Claisen rearrangement is markedly accelerated by an arylsulfonylmethide substituent at position 2. The generality of this anion variant has been extensively examined (3 1 allyl vinyl ethers) with regard to substitution, stereochemistry, and anion-stabilizing groups. The reactions generally proceed in good yield and with high regio- and stereoselectivities. The regiochemical course of the reaction is independent of the ...