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Journal ArticleDOI

Synthetic and mechanistic studies of the retro-Claisen rearrangement: an example of cation acceleration of a [3,3]-sigmatropic rearrangement

01 Jul 1985-Journal of the American Chemical Society (American Chemical Society)-Vol. 107, Iss: 14, pp 4359-4362
About: This article is published in Journal of the American Chemical Society.The article was published on 1985-07-01. It has received 28 citations till now. The article focuses on the topics: Sigmatropic reaction & Claisen rearrangement.
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Journal ArticleDOI
TL;DR: In this article, the photochemical reaction of transition metal boryl complexes of the type Cp*M(CO)nB(OR)2 (M = Fe, Ru, W) with alkanes to form alkylboronate esters was reported.
Abstract: We report the photochemical reaction of transition metal boryl complexes of the type Cp*M(CO)nB(OR)2 (M = Fe, Ru, W) with alkanes to form alkylboronate esters in yields as high as 85% for reaction ...

143 citations

Book ChapterDOI
01 Jan 1991
TL;DR: In this paper, a survey of variants of the Claisen rearrangement that are of general use in stereoselective organic synthesis is presented, highlighting the influence of steric and electronic parameters on transition state geometries.
Abstract: This article surveys variants of the Claisen rearrangement that are of general use in stereoselective organic synthesis. Recent results concerning the influence of steric and electronic parameters on transition state geometries are highlighted. The impact of the Claisen methodology in modern synthetic strategy and its application for the preparation of highly functionalized derivatives is exemplified.

100 citations

Journal ArticleDOI
TL;DR: An enantioselective total synthesis of the diterpenoid natural product (+)-salvileucalin B is reported, with key findings include a copper-catalyzed arene cyclopropanation reaction to provide the unusual norcaradiene core and a reversible retro-Claisen rearrangement of a highly functionalized nor caradiene intermediate.
Abstract: An enantioselective total synthesis of the diterpenoid natural product (+)-salvileucalin B is reported. Key findings include a copper-catalyzed arene cyclopropanation reaction to provide the unusual norcaradiene core and a reversible retro-Claisen rearrangement of a highly functionalized norcaradiene intermediate.

93 citations