Exploiting the enantioselectivity of Baeyer-Villiger monooxygenases via boron oxidation


Autoria(s): Brondani, Patricia B.; Dudek, Hanna; Reis, Joel S.; Fraaije, Marco W.; Andrade, Leandro Helgueira de
Contribuinte(s)

UNIVERSIDADE DE SÃO PAULO

Data(s)

25/10/2013

25/10/2013

2012

Resumo

The enantioselective carbon-boron bond oxidation of several chiral boron-containing compounds by Baeyer-Villiger monooxygenases was evaluated. PAMO and M446G PAMO conveniently oxidized 1-phenylethyl boronate into the corresponding 1-(phenyl)ethanol (ee = 82-91%). Cyclopropyl boronic esters were also oxidized but with no enantioselectivity. beta-Boryl carboxylic esters were not oxidized by any BVMOs. (C) 2012 Elsevier Ltd. All rights reserved.

CNPq

CNPq

CAPES

CAPES

FAPESP

FAPESP

Identificador

TETRAHEDRON-ASYMMETRY, OXFORD, v. 23, n. 9, pp. 703-708, MAY 15, 2012

0957-4166

http://www.producao.usp.br/handle/BDPI/36103

10.1016/j.tetasy.2012.05.004

http://dx.doi.org/10.1016/j.tetasy.2012.05.004

Idioma(s)

eng

Publicador

PERGAMON-ELSEVIER SCIENCE LTD

OXFORD

Relação

TETRAHEDRON-ASYMMETRY

Direitos

closedAccess

Copyright PERGAMON-ELSEVIER SCIENCE LTD

Palavras-Chave #CROSS-COUPLING REACTION #CYCLOHEXANONE OXYGENASE #PHENYLACETONE MONOOXYGENASE #1-ALKENYL HALIDES #VINYL PHOSPHATES #ESTERS #BIOCATALYSTS #BIS(PINACOLATO)DIBORON #IODIDES #ACID #CHEMISTRY, INORGANIC & NUCLEAR #CHEMISTRY, ORGANIC #CHEMISTRY, PHYSICAL
Tipo

article

original article

publishedVersion