A convenient resolution of pipecolic acid using a metal complex as the chiral auxiliary

Julia L. Clement; Peter Leverett; Robert S. Vagg; Peter A. Williams

A convenient resolution of pipecolic acid using a metal complex as the chiral auxiliary

Julia L. Clement, Peter Leverett, Robert S. Vagg, Peter A. Williams

Research output: Contribution to journal › Article

2 Citations (Scopus)

Abstract

Optically pure enantiomers of pipecolic acid are conveniently prepared in high yield by reacting the racemate with ÃŽâ€º-ÃŽÂ²-[Co(R,R-picchxn)Cl2]+ (picchxn = N,N'-di(2-picolyl)1,2-diaminocyclohexane) and crystallization of pure internal diastereoisomers as perchlorate salts. Subsequent reactions give the free acid of either hand. The stereochemical course of the resolution is established unambiguously by a single-crystal X-ray analysis of one intermediate and a combination of CD and 1H NMR measurements.

Original language	English
Number of pages	6
Journal	Journal of Coordination Chemistry
Publication status	Published - 2007

Keywords

internal diastereoisomer
pipecolic acid
resolution
x-ray structure
x-rays

Cite this

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title = "A convenient resolution of pipecolic acid using a metal complex as the chiral auxiliary",

abstract = "Optically pure enantiomers of pipecolic acid are conveniently prepared in high yield by reacting the racemate with {\~A}{\v Z}{\^a}€º-{\~A}{\v Z}{\^A}²-[Co(R,R-picchxn)Cl2]+ (picchxn = N,N'-di(2-picolyl)1,2-diaminocyclohexane) and crystallization of pure internal diastereoisomers as perchlorate salts. Subsequent reactions give the free acid of either hand. The stereochemical course of the resolution is established unambiguously by a single-crystal X-ray analysis of one intermediate and a combination of CD and 1H NMR measurements.",

keywords = "internal diastereoisomer, pipecolic acid, resolution, x-ray structure, x-rays",

author = "Clement, {Julia L.} and Peter Leverett and Vagg, {Robert S.} and Williams, {Peter A.}",

year = "2007",

language = "English",

journal = "Journal of Coordination Chemistry",

issn = "0095-8972",

publisher = "Taylor & Francis",

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TY - JOUR

T1 - A convenient resolution of pipecolic acid using a metal complex as the chiral auxiliary

AU - Clement, Julia L.

AU - Leverett, Peter

AU - Vagg, Robert S.

AU - Williams, Peter A.

PY - 2007

Y1 - 2007

N2 - Optically pure enantiomers of pipecolic acid are conveniently prepared in high yield by reacting the racemate with ÃŽâ€º-ÃŽÂ²-[Co(R,R-picchxn)Cl2]+ (picchxn = N,N'-di(2-picolyl)1,2-diaminocyclohexane) and crystallization of pure internal diastereoisomers as perchlorate salts. Subsequent reactions give the free acid of either hand. The stereochemical course of the resolution is established unambiguously by a single-crystal X-ray analysis of one intermediate and a combination of CD and 1H NMR measurements.

AB - Optically pure enantiomers of pipecolic acid are conveniently prepared in high yield by reacting the racemate with ÃŽâ€º-ÃŽÂ²-[Co(R,R-picchxn)Cl2]+ (picchxn = N,N'-di(2-picolyl)1,2-diaminocyclohexane) and crystallization of pure internal diastereoisomers as perchlorate salts. Subsequent reactions give the free acid of either hand. The stereochemical course of the resolution is established unambiguously by a single-crystal X-ray analysis of one intermediate and a combination of CD and 1H NMR measurements.

KW - internal diastereoisomer

KW - pipecolic acid

KW - resolution

KW - x-ray structure

KW - x-rays

UR - http://handle.uws.edu.au:8081/1959.7/34086

M3 - Article

SN - 0095-8972

JO - Journal of Coordination Chemistry

JF - Journal of Coordination Chemistry

ER -

A convenient resolution of pipecolic acid using a metal complex as the chiral auxiliary

Abstract

Keywords

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