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Evidence for a boroxinate based Bronsted acid derivative of VAPOL as the active catalyst in the catalytic asymmetric aziridination reaction.

ABSTRACT: Studies are described that were designed to determine the structure of the active catalyst in the asymmetric catalytic aziridination of imines with ethyl diazoacetate (AZ reaction). Evidence suggests that the active catalyst contains a boroxine ring in which one of the three boron atoms is spiro-fused with the two phenol groups of the VAPOL ligand. (11)B and (1)H NMR evidence supports the boroxinate structure B in which the counterion to the boroxinate is the protonated form of the imine. The boroxinate structure is also supported by two solid state structures of a VAPOL boroxinate in which the gegen cation is tetramethyl ammonium and 4-dimethylaminopyridinium.

SUBMITTER: Hu G

PROVIDER: S-EPMC2783389 | biostudies-literature | 2009 Nov

REPOSITORIES: biostudies-literature

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Evidence for a boroxinate based Brønsted acid derivative of VAPOL as the active catalyst in the catalytic asymmetric aziridination reaction.

Hu Gang G Huang Li L Huang Rui H RH Wulff William D WD

Journal of the American Chemical Society 20091101 43

Studies are described that were designed to determine the structure of the active catalyst in the asymmetric catalytic aziridination of imines with ethyl diazoacetate (AZ reaction). Evidence suggests that the active catalyst contains a boroxine ring in which one of the three boron atoms is spiro-fused with the two phenol groups of the VAPOL ligand. (11)B and (1)H NMR evidence supports the boroxinate structure B in which the counterion to the boroxinate is the protonated form of the imine. The bo ...[more]

PMID: 19813716

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