Publication

Palladium-catalyzed conversion of beta,gamma-unsaturated silyl sulfinates into (E)-alkenes: Asymmetric synthesis of polypropionate fragments

Pierre Vogel
2004
Journal Articles

Abstract

At low temperature, 1-alkoxy-1,3-dienes add to sulfur dioxide activated by a Lewis or protic acid generating zwitterionic intermediates that can be quenched by enoxysilanes. The resulting beta,gamma-unsaturated silyl sulfinates can be desilylated by 1:1 Pd(OAc)(2)/PPh3 catalyst, liberating the corresponding beta,gamma-unsaturated sulfinic acids that undergo smooth and highly stereoselective retro-ene eliminations of sulfur dioxide. The method has been applied to generate enantiomerically pure polypropionate fragments.

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https://infoscience.epfl.ch/entities/publication/0bcc1c12-50c7-4d56-b18f-4d357df03a07

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Pierre Vogel
2004
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/0bcc1c12-50c7-4d56-b18f-4d357df03a07

About this result

Related concepts (26)

Sulfur dioxide

Sulfur dioxide (IUPAC-recommended spelling) or sulphur dioxide (traditional Commonwealth English) is the chemical compound with the formula SO2. It is a toxic gas responsible for the odor of burnt matches. It is released naturally by volcanic activity and is produced as a by-product of copper extraction and the burning of sulfur-bearing fossil fuels. SO2 is a bent molecule with C2v symmetry point group. A valence bond theory approach considering just s and p orbitals would describe the bonding in terms of resonance between two resonance structures.

Sulfur

Sulfur (also spelled sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula S8. Elemental sulfur is a bright yellow, crystalline solid at room temperature. Sulfur is the tenth most abundant element by mass in the universe and the fifth most on Earth. Though sometimes found in pure, native form, sulfur on Earth usually occurs as sulfide and sulfate minerals.

Sulfuric acid

Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, and hydrogen, with the molecular formula . It is a colorless, odorless, and viscous liquid that is miscible with water. Pure sulfuric acid does not occur naturally due to its strong affinity to water vapor; it is hygroscopic and readily absorbs water vapor from the air.

Related publications (5)

Palladium-catalyzed conversion of beta,gamma-unsaturated silyl sulfinates into (E)-alkenes: Asymmetric synthesis of polypropionate fragments

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