Publication

New carbon-carbon bond formation through oxyallylation of enoxysilanes with sulfur dioxide adduct of 1-methoxybutadiene. Stereoselective synthesis of (Z)-4-methoxy-6-oxoalk-2-enyl methyl sulfones

Pierre Vogel
1997
Journal Articles

Abstract

Mixtures of 1-methoxybutadiene, trimethylsilyl enol ethers, SO2 and a Lewis acid catalyst generate trimethylsilyl (Z)-4-methoxy-6-oxoalk-2-enesulfinates that can be converted into 4-methoxy-6-oxoalk-2-enyl methyl sulfones and 5-alkyl-4-methoxy-6-oxoalk-2-enyl methyl sulfones with 100% (Z) selectivity and good syn diastereoselectivity for the 5-alkyl and 4-methoxy substituents. (C) 1997 Elsevier Science Ltd.

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Pierre Vogel
1997
Journal Articles

Abstract

Official source

Related concepts (17)

Enantioselective synthesis

Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts." Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer.

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one of the most important branches of organic chemistry. There are several main areas of research within the general area of organic synthesis: total synthesis, semisynthesis, and methodology.

Stereoselectivity

In chemistry, stereoselectivity is the property of a chemical reaction in which a single reactant forms an unequal mixture of stereoisomers during a non-stereospecific creation of a new stereocenter or during a non-stereospecific transformation of a pre-existing one. The selectivity arises from differences in steric and electronic effects in the mechanistic pathways leading to the different products. Stereoselectivity can vary in degree but it can never be total since the activation energy difference between the two pathways is finite: both products are at least possible and merely differ in amount.

Related publications (1)

New carbon-carbon bond formation through oxyallylation of enoxysilanes with sulfur dioxide adduct of 1-methoxybutadiene. Stereoselective synthesis of (Z)-4-methoxy-6-oxoalk-2-enyl methyl sulfones

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