Issue 39, 2013
From the journal:

Organic & Biomolecular Chemistry

Shvo's catalyst in chemoenzymatic dynamic kinetic resolution of amines – inner or outer sphere mechanism?†

Boniek G. Vaz,a   Cintia D. F. Milagre,b   Marcos N. Eberlin*c  and  Humberto M. S. Milagre*b  

* Corresponding authors

a Institute of Chemistry, Federal University of Goiás, Campus Samambaia, Caixa Postal 131, Goiânia, Goiás, Brazil

b Department of Organic Chemistry, Institute of Chemistry, Univ. Estadual Paulista UNESP, Araraquara, SP, Brazil
E-mail: humbertomilagre@iq.unesp.br

c ThoMSon Mass Spectrometry Laboratory – Institute of Chemistry, University of Campinas UNICAMP, Campinas, SP, Brazil
E-mail: eberlin@iq.unicamp.br

Abstract

Evidence is provided for the inner-sphere mechanism with actual metal coordination of the racemic amine in the crucial hydrogen transfer step promoted by Shvo's catalyst of the chemoenzymatic dynamic kinetic resolution (DKR) of amines. Key intermediates involved in this H-transfer step were intercepted and continuously monitored by electrospray ionization mass spectrometry (ESI-MS) and characterized by their dissociation chemistries via ESI-MS/MS.

Graphical abstract: Shvo's catalyst in chemoenzymatic dynamic kinetic resolution of amines – inner or outer sphere mechanism?

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Article information

DOI
https://doi.org/10.1039/C3OB41318G
Article type
Communication
Submitted
27 Jun 2013
Accepted
10 Aug 2013
First published
14 Aug 2013

Org. Biomol. Chem., 2013,11, 6695-6698

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Shvo's catalyst in chemoenzymatic dynamic kinetic resolution of amines – inner or outer sphere mechanism?

B. G. Vaz, C. D. F. Milagre, M. N. Eberlin and H. M. S. Milagre, Org. Biomol. Chem., 2013, 11, 6695 DOI: 10.1039/C3OB41318G

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