Stereoselective Synthesis of Homofarnesenes: Establishment of an Efficient Method for the Stereoselective Preparation of Acyclic Tetrasubstituted Olefins

A new method for the stereoselective synthesis of tetrasubstituted olefins is described. β-Ketophosphonates are alkylated via conventional methods, and a Grignard reagent is used to diastereoselectively add to the carbonyl group of the resulting intermediates. The elimination of hydroxyl phosphonate...

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Bibliographic Details
Published inACS omega Vol. 3; no. 4; pp. 4551 - 4556
Main Authors Yin, Wenhao, Liang, Weihong, Guo, Liping, Lei, Jiaheng, Qiu, Fayang G
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 30.04.2018
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Summary:A new method for the stereoselective synthesis of tetrasubstituted olefins is described. β-Ketophosphonates are alkylated via conventional methods, and a Grignard reagent is used to diastereoselectively add to the carbonyl group of the resulting intermediates. The elimination of hydroxyl phosphonates yielded the desired tetrasubstituted olefins in a stereoselective manner. Thus, homofarnesenes of fire ant trail pheromones have been synthesized efficiently using this strategy.
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ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.8b00439