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Preparation and Reaction Chemistry of Novel Silicon-Substituted 1,3-Dienes.

ABSTRACT: 2-Silicon-substituted 1,3-dienes containing non transferrable groups known to promote transmetallation were prepared by Grignard chemistry and enyne metathesis. These dienes participated in one pot metathesis/Diels-Alder reactions in regio- and diastereoselective fashions. Electron-rich alkenes showed the fastest rates in metathesis reactions, and ethylene, a commonly used metathesis promoter slowed enyne metathesis. 2-Pyridyldimethylsilyl and 2-thienyldimethylsilyl substituted Diels-Alder cycloadducts participated in cross-coupling chemistry and the 2-thienyldimethylsilyl substituted cycloadducts underwent cross-coupling under very mild reaction conditions.

SUBMITTER: Choudhury PP

PROVIDER: S-EPMC6332380 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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Preparation and Reaction Chemistry of Novel Silicon-Substituted 1,3-Dienes.

Choudhury Partha P PP Welker Mark E ME

Molecules (Basel, Switzerland) 20150916 9

2-Silicon-substituted 1,3-dienes containing non transferrable groups known to promote transmetallation were prepared by Grignard chemistry and enyne metathesis. These dienes participated in one pot metathesis/Diels-Alder reactions in regio- and diastereoselective fashions. Electron-rich alkenes showed the fastest rates in metathesis reactions, and ethylene, a commonly used metathesis promoter slowed enyne metathesis. 2-Pyridyldimethylsilyl and 2-thienyldimethylsilyl substituted Diels-Alder cyclo ...[more]

PMID: 26389877

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