Single-isomer tetrasubstituted olefins from regioselective and stereospecific palladium-catalyzed coupling of beta-chloro-alpha-iodo-alpha,beta-unsaturated esters

The Journal of Organic Chemistry
Alison B LemayWilliam W Ogilvie

Abstract

The efficient regioselective and stereospecific synthesis of tetrasubstituted olefins using a mild and convenient method is disclosed. 2-Alkynyl esters are selectively converted to E-beta-chloro-alpha-iodo-alpha,beta-unsaturated esters by exposure to Bu4NI in refluxing dichloroethane. These products are produced cleanly, regio- and stereoselectively, and in high yields. Single-isomer tetrasubstituted olefins bearing four different carbon substituents are then synthesized by sequential palladium-catalyzed coupling reactions. Selectivity results from reactivity differences in the intermediate substrates.

References

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Citations

Sep 28, 2010·Chemical Communications : Chem Comm·Zhengwang ChenChaorong Qi
Aug 8, 2015·The Journal of Organic Chemistry·Mirza A SaputraRendy Kartika
Sep 6, 2006·Angewandte Chemie·Thomas B PoulsenKarl Anker Jørgensen
May 15, 2008·Angewandte Chemie·Thomas B PoulsenKarl Anker Jørgensen
Apr 26, 2019·Chemistry : a European Journal·Junliang WuNaohiko Yoshikai
Jun 6, 2019·Organic & Biomolecular Chemistry·Ritush Kumar, Radhey M Singh
Sep 16, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yuichiro Ashida, Yoo Tanabe
Nov 2, 2007·Chemical Reviews·Alison B Flynn, William W Ogilvie
Feb 20, 2007·Chemical Reviews·Rafael Chinchilla, Carmen Najera
Jul 5, 2008·The Journal of Organic Chemistry·He HuangKaixian Chen
Apr 28, 2009·The Journal of Organic Chemistry·Jie ChenXiao-Ping Cao
Aug 21, 2010·Organic Letters·Benjamin DarsesJean-François Poisson
Apr 19, 2011·The Journal of Organic Chemistry·Jun-Tao ZhangXiao-Ping Cao

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