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

Author: Clement Julia L.   Leverett Peter   Vagg Robert S.   Williams Peter A.  

Publisher: Taylor & Francis Ltd

ISSN: 0095-8972

Source: Journal of Coordination Chemistry, Vol.60, Iss.16, 2007-08, pp. : 1789-1794

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Abstract

Optically pure enantiomers of pipecolic acid are conveniently prepared in high yield by reacting the racemate with Λ-β-[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.

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