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

*Corresponding author for this work

Research output: Contribution to journalArticle

2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1789-1794
Number of pages6
JournalJournal of Coordination Chemistry
Volume60
Issue number16
DOIs
Publication statusPublished - Aug 2007

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