Synthesis of methyl N-Boc-(2S,4R)-4-methylpipecolate |
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Authors: | Hung Kuo-Yuan Harris Paul W R Brimble Margaret A |
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Affiliation: | Department of Chemistry, The University of Auckland, 23 Symonds Street, Auckland, New Zealand. |
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Abstract: | An efficient stereoselective synthesis of fully protected (2S,4R)-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 OsO(4)/NaIO(4) followed by immediate intramolecular cyclization afforded an enamine that was then subjected to hydrogenation to give the final compound in 23% yield over 10 steps. |
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