Volume 31, Issue 12
Natural Products
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ChemInform Abstract: Synthesis of Chiral Nonracemic 4-trans-Substituted Pipecolic Acid Derivatives.

Terence P. Keenan

Terence P. Keenan

ARIAD Gene Ther., Inc., Cambridge, MA 02139, USA

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David Yaeger

David Yaeger

ARIAD Gene Ther., Inc., Cambridge, MA 02139, USA

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Dennis A. Holt

Dennis A. Holt

ARIAD Gene Ther., Inc., Cambridge, MA 02139, USA

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First published: 09 June 2010

Abstract

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ChemInform Abstract

Treatment of the piperidine (I) with CO2 offers a useful method to prepare the acid (III). L-Tyrosine hydrazide-mediated resolution of (III) and related compounds leads to 4-cis-D-pipecolic acid derivatives which can easily be transformed into 4-trans-L-pipecolic acids.

chemical structure image

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