A new chiral derivatizing agent for ee determination of 1,2-diols via H-1 NMR is described. (S)-(+)-N-Acetylphenylglycineboronic acid (1) is synthesized in enantiomerically pure form; its reaction with chiral diols quantitatively yields cyclic boronic esters 5a-g. The latter show a remarkably high diastereodifferentiation of proton NMR signals useful for de determination.
(S)-(+)-N-acetylphenylglycineboronic acid: A chiral derivatizing agent for Ee determination of 1,2-diols / Caselli, Emilia; Danieli, Chiara; Morandi, Stefania; B., Bonfiglio; Forni, Arrigo; Prati, Fabio. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 5:25(2003), pp. 4863-4866. [10.1021/ol0359970]
(S)-(+)-N-acetylphenylglycineboronic acid: A chiral derivatizing agent for Ee determination of 1,2-diols
CASELLI, Emilia;DANIELI, Chiara;MORANDI, Stefania;FORNI, Arrigo;PRATI, Fabio
2003
Abstract
A new chiral derivatizing agent for ee determination of 1,2-diols via H-1 NMR is described. (S)-(+)-N-Acetylphenylglycineboronic acid (1) is synthesized in enantiomerically pure form; its reaction with chiral diols quantitatively yields cyclic boronic esters 5a-g. The latter show a remarkably high diastereodifferentiation of proton NMR signals useful for de determination.
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