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Your search keyword '"M. A. Vadillo"' showing total 2 results
Start Over Author "M. A. Vadillo" Journal tetrahedron: asymmetry
2 results on '"M. A. Vadillo"'

1. Synthesis of enantiomerically pure 1,3-diols by stereoselective reduction of β-ketosulfoxides. Influence of a stereogenic hydroxylic centre at the δ-position

Author

M. Carmen Maestro, Ana M. González-Vadillo, and José L. García Ruano

Subjects
Inorganic Chemistry, chemistry.chemical_compound, Chemistry, Stereochemistry, Organic Chemistry, Stereoselectivity, Physical and Theoretical Chemistry, Carbonyl group, Catalysis, Stereocenter
Abstract

The influence of the stereogenic hydroxylic carbon at the δ-position of the carbonyl group in 1,5-bis( p -tolylsulfinyl)-4-hydroxy-2-pentanone 1 and 2,6-bis( p -tolylsulfinyl)-5-hydroxy-3-hexanones 2 on the stereochemical course of DIBALH and DIBALH/ZnBr 2 reductions has been studied. In contrast with the DIBALH reductions of β-hydroxyketones, that are monitored by the hydroxylic stereogenic carbon, the presence of the sulfinyl group determines a complete 1,3-induction of the sulfur centre.

Published
1997
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2. Synthesis of enantiomerically pure β-hydroxy-γ-sulfinylaldehyde dimethyl acetals

Author

Ana M. González-Vadillo, David Barros, José L. García Ruano, and M. Carmen Maestro

Subjects
Inorganic Chemistry, chemistry.chemical_classification, chemistry, Organic Chemistry, Organic chemistry, chemistry.chemical_element, Stereoselectivity, Lithium, Physical and Theoretical Chemistry, Catalysis, Alkyl
Abstract

Lithium alkyl p -tolylsulfinyl anions generated from 2 or 3 react with methyl 3,3-dimethoxypropanoate ( 1 ) yielding the corresponding β-ketosulfoxides 4 and 5 respectively. The presence of two methoxy groups in the δ-position of these β-ketosulfoxides has little or no influence on the stereoselectivity of DIBAL and DIBAL/ZnX 2 reductions, allowing the synthesis of the title acetals in high diastereoisomeric excess.

Published
1996
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