The use of chiral auxiliaries prepared from (-)-β-pinene in stereoselective reduction of β-ketobutyrates

Article abstract of DOI:10.1080/00397910008087342

Chiral auxiliaries previously prepared from (-)-β-pinene (3), alcohols 5a-e and 6, were transformed into β-ketobutyrates 7a-e and 8 respectively. These compounds were stereoselectively reduced by NaBH₄ in the presence of additives (MnCl₂ or CaCl₂), leading to the corresponding β-hydroxy butyrates 10a-e and 11 in good chemical yield and poor to moderate stereoselectivities (de 0%-60%). The configuration at the newly generated stereogenic center in 10a was determined to be S through its transformation into S-(+)-butanediol.

Full text of DOI:10.1080/00397910008087342

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Synthetic Communications: An
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The Use of Chiral Auxiliaries
Prepared from (-)-β-Pinene in
Stereoselective Reduction of β-
Ketobutyrates
Karla G. Alencar a , Ubiracir F.L. Filho a , Mário L. A.
A. Vasconcellos a & Paulo R.R. Costa b
a Laboratório H1-029 , Brazil E-mail:
b Laboratório de Sintese Assimétrica (LASA), Núcleo
de Pesquisas de Produtos Naturais, Universidade
Federal do Rio de Janeiro, Centro de Ciěncias
da Saúde, Bloco H, Ilha da Cidade Universitária ,
21941--590, RJ, Rio de Janeiro, Brazil E-mail:
Published online: 04 Dec 2007.
To cite this article: Karla G. Alencar , Ubiracir F.L. Filho , Mário L. A. A. Vasconcellos
& Paulo R.R. Costa (2000) The Use of Chiral Auxiliaries Prepared from (-)-β-Pinene
in Stereoselective Reduction of β-Ketobutyrates, Synthetic Communications: An
International Journal for Rapid Communication of Synthetic Organic Chemistry, 30:3,
455-468, DOI: 10.1080/00397910008087342
To link to this article: http://dx.doi.org/10.1080/00397910008087342
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