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Updated: Aug 16, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

アリルアンモニアムイリドの非対称[2,3]-シグマトロピク再配置

Jan Blid1, Olaf Panknin, Peter Somfai

  • 1Organic Chemistry, KTH Chemistry, Royal Institute of Technology, SE-100 44 Stockholm, Sweden.

Journal of the American Chemical Society
|June 30, 2005
PubMed
まとめ

新しい非対称ルイス酸法により, [2,3]-シグマトロピク再配列によるアリルアミンからホモアリルアミンのエナチオセレクティブ合成が可能である. このアプローチは,キラルアミン化合物を効率的に作成するための強力なツールを提供します.

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not observed.
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