Tetrahedron letters

Tandem cyclisation and [2, 3]-Stevens rearrangement to 2-substituted pyrrolidines

SC Smith, PD Bentley

Index: Smith, Stephen C; Bentley, Philip D Tetrahedron Letters, 2002 , vol. 43, # 5 p. 899 - 902

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Citation Number: 16

Abstract

Reaction of N-methylallylamine with diethyl meso-2, 5-dibromoadipate in DMF at ambient temperature in the presence of potassium carbonate led directly to the two diastereomers of diethyl 2-allyl-N-methylpyrrolidine-2, 5-dicarboxylate. The reaction proceeds via a [2, 3]- sigmatropic Stevens rearrangement, which occurred spontaneously under the reaction conditions. This gave a higher yield under milder conditions than the traditional Stevens ...