Lipase-Catalyzed Highly Enantioselective Kinetic Resolution of Boron-Containing Chiral Alcohols


Autoria(s): ANDRADE, Leandro H.; BARCELLOS, Thiago
Contribuinte(s)

UNIVERSIDADE DE SÃO PAULO

Data(s)

20/10/2012

20/10/2012

2009

Resumo

The first application of enzymes as catalysts to obtain optically pure boron compounds is described. The kinetic resolution of boron-containing chiral alcohols via enantioselective transesterification catalyzed by lipases was studied. Aromatic, allylic, and aliphatic secondary alcohols containing a boronate ester or boronic acid group were resolved by lipase from Candida antartica (CALB), and excellent E values (E > 200) and high enantiomeric excesses (up to >99%) of both remaining substrates and acetylated product were obtained.

University of Pennsylvania

University of Pennsylvania

FAPESP (State of Sao Paulo Research Foundation)

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)

CNPq (National Counsel of Technological and Scientific Development)

Identificador

ORGANIC LETTERS, v.11, n.14, p.3052-3055, 2009

1523-7060

http://producao.usp.br/handle/BDPI/31173

10.1021/ol901091f

http://dx.doi.org/10.1021/ol901091f

Idioma(s)

eng

Publicador

AMER CHEMICAL SOC

Relação

Organic Letters

Direitos

restrictedAccess

Copyright AMER CHEMICAL SOC

Palavras-Chave #NEUTRON-CAPTURE THERAPY #CROSS-COUPLING REACTION #SECONDARY ALCOHOLS #ORGANIC-SYNTHESIS #CHEMISTRY #INHIBITORS #Chemistry, Organic
Tipo

article

original article

publishedVersion