Synthesis of 3-methoxycycloheptatrienones

VA Roberts, ME Garst, NE Torres

Index: Roberts, Victoria A.; Garst, Michael E.; Torres, Norman E. Journal of Organic Chemistry, 1984 , vol. 49, # 6 p. 1136 - 1138

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Citation Number: 5

Abstract

A probable mechanism for the unexpected formation of N-acetylphenylalanine in the hydrogenolysis reaction is shown in Scheme I. The key to this mechanism is the formation of the oxazolidine 2-a generally accepted common intermediate for the 0 s N acyl migration in the acylated amino alcohol system. 8 The reduction of this cyclic intermediate 2 leads to the observed acyl shift hydrogenolysis product le. 9 The two minor components, ...