Mimicking the reaction of phenylalanine ammonia lyase by a synthetic model

M Rettig, A Sigrist, J Rétey

Index: Rettig, Martin; Sigrist, Andreas; Retey, Janos Helvetica Chimica Acta, 2000 , vol. 83, # 9 p. 2246 - 2265

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Citation Number: 21

Abstract

Results.±Synthesis of Model 7 (Scheme 2): Model 7 comprised a cyclohexanamine substituted with a Ph group in position 2 and an α, β-unsaturated amide moiety in position 3. The starting material for its synthesis was (Æ)-2-phenylcyclohexanone (1) which was prepared from commercial (Æ)-2-chlorocyclohexanone and phenylmagnesium bromide by a modified method of Newman and Farbman [15][16](Scheme 2). Bromination of 1 by N- ...