Asymmetric alkylation of. beta.-keto esters with optically active sulfonium salts

K Umemura, H Matsuyama, N Watanabe…

Index: Umemura, Kazuyuki; Matsuyama,Haruo; Watanabe, Nobuko; Kobayashi, Michio; Kamigata, Nobumasa Journal of Organic Chemistry, 1989 , vol. 54, # 10 p. 2374 - 2383

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Citation Number: 41

Abstract

Alkylation of the cyclic@-keto ester 2-(methoxycarbonyl)-l-indanone (2) with racemic alkylsulfonium salts la-h gave 2-alkylindanones 3 and 4 in 60-9670 yields. The relative reactivities of the alkyl substituents of aryldialkylsulfonium salts le and If were quite different from those in SN2 alkylations. Asymmetric induction occurred upon alkylation of 2 with optically active sulfonium salts.(R)-2-Ethyl-2-(methoxycarbonyl) cyclohexanone (11) was ...