Synthesis of methyl N-Boc-(2 S, 4 R)-4-methylpipecolate

K Hung, PWR Harris, MA Brimble

Index: Hung, Kuo-Yuan; Harris, Paul W. R.; Brimble, Margaret A. Journal of Organic Chemistry, 2010 , vol. 75, # 24 p. 8728 - 8731

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Citation Number: 16

Abstract

An efficient stereoselective synthesis of fully protected (2 S, 4 R)-4-methylpipecolic acid has been developed. The synthesis was achieved by initial asymmetric α-alkylation of glycine with a chiral iodide, affording the linear precursor as a single stereoisomer. Subsequent aldehyde formation using OsO4/NaIO4 followed by immediate intramolecular cyclization afforded an enamine that was then subjected to hydrogenation to give the final compound ...