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Enzymatic and chromatographic resolution procedures applied to the synthesis of the phosphoproline enantiomers

AuthorsArizpe, Alicia ; Rodríguez-Mata, María; Sayago, Francisco J. ; Pueyo, María J.; Gotor, Vicente; Jiménez, Ana I. ; Gotor-Fernández, Vicente; Cativiela, Carlos
Issue Date2015
CitationTetrahedron Asymmetry 26(24): 1469-1477 (2015)
AbstractThe preparation of enantiomerically pure pyrrolidine-2-phosphonic acid (phosphoproline, Pro) has been addressed through the synthesis of suitable racemates and subsequent resolution by independent enzyme-catalyzed and chiral HPLC methods. First, racemic phosphoproline derivatives bearing the necessary protecting groups have been synthesized in excellent global yields starting from inexpensive materials. Preparative HPLC resolution of the N-Cbz-protected aminophosphonate on a cellulose-based column allowed the isolation of enantiomerically pure enantiomers on a gram scale. Enzyme-catalyzed alkoxycarbonylation of the aminophosphonate was studied using different lipases, solvents, and carbonates. Candida antarctica lipase type A (CAL-A) provided the highest enantioselectivity when combined with benzyl 3-methoxyphenyl carbonate.
Identifiersdoi: 10.1016/j.tetasy.2015.10.016
e-issn: 1362-511X
issn: 0957-4166
Appears in Collections:(ISQCH) Artículos
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