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Vanadium-controlled crystallization of stereoisomers of NBu4[VO2(N-salicylidene-isoleucinato)] through epimerization

, : Vanadium-controlled crystallization of stereoisomers of NBu4[VO2(N-salicylidene-isoleucinato)] through epimerization. Chemistry 20(29): 8872-8875

Reported herein is a simple synthetic and crystallization procedure for sequential isolation of two stereoisomers of isoleucine-derived vanadium(V) complexes from a racemic mixture with three stereogenic centers and therefore eight hypothetical species. The products of this crystallization were characterized by electronic and vibrational circular dichroism, NMR spectroscopy, and polarimetry to compare the chiroptic properties of the enantiomerically pure analogues prepared from L-isoleucine and D-allo-isoleucine. NMR studies pointed to the yet unobserved phenomenon of vanadium-catalyzed epimerization of isoleucine.


PMID: 24938223

DOI: 10.1002/chem.201403125

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