Tetrahedron Letters

Direct diastereoselective synthesis of (±)-cis-and (±)-trans-4-methylpipecolic acid and derivatives

J Cossy, D Belotti

Index: Cossy, Janine; Belotti, Damien Tetrahedron Letters, 2001 , vol. 42, # 11 p. 2119 - 2120

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Citation Number: 10

Abstract

It has been reported than the N-tert-butoxycarbonyl group (N-Boc) is an effective directing group for the α-lithiation of piperidines 4 and that the more thermodynamically stable isomer is the transN-Boc 4-substituted pipecolic acid derivatives. 5., and As alkyl (±)-trans-4-methylpipecolate was needed to synthesize argatroban, 6., , , , , , , , , , , , and carboxylation of 4-methylpiperidine was envisaged. Although, alkyl chloroformates as electrophiles were reported to give very ...