Highly stereoselective prins cyclization of silylmethyl-substituted cyclopropyl carbinols to 2,4,6-trisubstituted tetrahydropyrans

Journal of the American Chemical Society
Veejendra K Yadav, Naganaboina Vijaya Kumar

Abstract

The homoallyl cation formed from a cyclopropyl carbinol that was vicinally substituted by a silylmethyl function underwent smooth Prins cyclization with aldehydes and ketones to form 2,4,6-trisubstituted tetrahydropyrans with very high stereoselectivity.

References

Aug 23, 2001·Journal of the American Chemical Society·D J Kopecky, S D Rychnovsky
Nov 1, 1996·The Journal of Organic Chemistry·Leo A. Paquette, Jinsung Tae
May 16, 1997·The Journal of Organic Chemistry·Scott D. RychnovskyUday R. Khire
May 2, 2002·Journal of the American Chemical Society·Roger W AlderMark T Oakley
Jul 18, 2002·Chemical Communications : Chem Comm·Veejendra K Yadav, Rengarajan Balamurugan
Apr 10, 2003·Chemical Reviews·Hans-Ulrich Reissig, Reinhold Zimmer
Apr 26, 2003·Organic Letters·David J Hart, Chad E Bennett
Jul 5, 2003·Organic Letters·Conor St J BarryChristine L Willis
Oct 2, 2003·Chemical Communications : Chem Comm·Yong Seo ChoMoon Ho Chang
Apr 3, 2004·The Journal of Organic Chemistry·Takehiko YoshimitsuHiroto Nagaoka
Jul 17, 2008·Angewandte Chemie·Veejendra K Yadav, Vardhineedi Sriramurthy

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Citations

Aug 8, 2008·Chemical Communications : Chem Comm·Veejendra K Yadav, Naganaboina Vijaya Kumar
Dec 6, 2008·Chemical Communications : Chem Comm·Divya Agrawal, Veejendra K Yadav
Aug 23, 2016·Journal of the American Chemical Society·Luping LiuBenjamin List
Oct 28, 2016·Journal of the American Chemical Society·Youwei XieBenjamin List
Aug 10, 2017·Organic & Biomolecular Chemistry·M Skvorcova, A Jirgensons
Aug 8, 2006·ChemMedChem·Pedro O MirandaVíctor S Martín
Mar 24, 2020·Organic & Biomolecular Chemistry·Birakishore PadhiDebendra K Mohapatra
May 28, 2015·Angewandte Chemie·Gavin Chit TsuiBenjamin List
Sep 21, 2013·Chemical Communications : Chem Comm·Lu GaoZhenlei Song
Mar 23, 2011·Organic & Biomolecular Chemistry·Somasekhar BondalapatiAnil K Saikia
Jun 3, 2014·Chemical Communications : Chem Comm·Claudia Lalli, Pierre van de Weghe
Oct 6, 2012·Organic & Biomolecular Chemistry·Pipas SahaAnil K Saikia
Jul 17, 2009·Organic Letters·Binxun YuXuegong She
Sep 5, 2008·Journal of the American Chemical Society·Kevin B Bahnck, Scott D Rychnovsky
May 14, 2021·Beilstein Journal of Organic Chemistry·Asha BudakotiJagadish Khamrai
Aug 16, 2019·Organic Letters·Huai-Ri SunLing Zhou
Jun 4, 2015·Organic Letters·Marija SkvorcovaAigars Jirgensons
Sep 4, 2014·The Journal of Organic Chemistry·Paramartha GogoiAnil K Saikia
Aug 29, 2019·ACS Omega·Upasana BorthakurAnil K Saikia
Aug 26, 2006·The Journal of Organic Chemistry·Yajing Lian, Robert J Hinkle
Nov 19, 2004·Organic Letters·Veejendra K Yadav, Vardhineedi Sriramurthy

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