PtCl2-catalyzed cycloisomerizations of 5-en-1-yn-3-ol systems

Journal of the American Chemical Society
Youssef HarrakMax Malacria

Abstract

5-En-1-yn-3-ol substrates bearing a free hydroxyl group or an acyl group are highly versatile partners for PtCl2-catalyzed cycloisomerizations. Electrophilic activation of the alkyne moiety triggers at wish a hydride or an O-acyl migration yielding at the end to regioisomeric keto derivatives. The efficient preparation of Sabina ketone, an important monoterpene precursor, has been worked out.

References

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Apr 23, 2004·Organic Letters·Frédéric MarionMax Malacria

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Citations

Sep 8, 2005·Journal of the American Chemical Society·B A Bhanu PrasadRichmond Sarpong
Jan 5, 2008·Journal of the American Chemical Society·Alexander S DudnikVladimir Gevorgyan
Dec 1, 2006·Organic Letters·Christiane M Grisé, Louis Barriault
Feb 1, 2006·Chemical Communications : Chem Comm·Daniel KadzimirszGerald Dyker
Nov 12, 2009·Chemical Communications : Chem Comm·Chung-Meng ChaoVéronique Michelet
Sep 15, 2011·Beilstein Journal of Organic Chemistry·Alexandre PradalVéronique Michelet
Feb 28, 2013·Chemical Society Reviews·Roohollah Kazem Shiroodi, Vladimir Gevorgyan
Jun 17, 2016·Angewandte Chemie·Minqiang Jia, Shengming Ma
Mar 19, 2016·Chemistry : a European Journal·Alexis ArchambeauJanine Cossy
Jan 6, 2015·Chemistry : a European Journal·Ana M SanjuánRoberto Sanz
Aug 16, 2016·Chemical Communications : Chem Comm·Gen-Qiang ChenMin Shi
Jun 7, 2006·Chemistry : a European Journal·Cristina Nieto-OberhuberAntonio M Echavarren
Sep 21, 2006·Angewandte Chemie·Sylvain CoutyJanine Cossy
Jan 4, 2007·Chemistry : a European Journal·José Marco-Contelles, Elena Soriano
Mar 10, 2007·Angewandte Chemie·Nicolas Marion, Steven P Nolan
May 29, 2007·Chemistry : a European Journal·Nicolas MarionSteven P Nolan
Mar 5, 2008·Chemistry : a European Journal·Benedikt Crone, Stefan F Kirsch
Apr 3, 2008·Angewandte Chemie·Véronique MicheletJean-Pierre Genêt
Oct 23, 2009·Chemical Society Reviews·Alois Fürstner
Jul 31, 2010·Angewandte Chemie·Changkun LiJianbo Wang
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Dec 17, 2005·Chemistry : a European Journal·Cristina Nieto-OberhuberAntonio M Echavarren
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Apr 20, 2011·Chemistry : a European Journal·Charles FehrHorst Sommer
Jan 16, 2007·Chemical Communications : Chem Comm·Eloísa Jiménez-Núñez, Antonio M Echavarren

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