Optical resolution of N-(t-butoxycarbonyl)leucine through mixed ligand complex formation with (R)-N-(2-pyridylmethyl)pipecolatocopper(II)

Add time:07/18/2019    Source:sciencedirect.com

A copper(II) complex of (R)-N-(2-pyridylmethyl)pipecolate (pmpi) was prepared, and its structure was revealed by X-ray crystal structure analysis. Mixed ligand complexes were then prepared from this complex and (R)- and (S)-N-(t-butoxycarbonyl)leucinate (BocLeu). The (R)-BocLeu complex is less soluble in aqueous acetonitrile and more soluble in acetone than the (S)-BocLeu complex, and the reason was discussed on the basis of their structures. Recrystallization of the reaction mixture consisting of Cu(II) ion, pmpi, and (RS)-BocLeu from aqueous acetonitrile gave the (R)-BocLeu complex and that from acetone gave the (S)-BocLeu complex.

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