Stereoselective oxidative rearrangement of 2-aryl tryptamine derivatives

Organic Letters
Mohammad MovassaghiJames A Ashenhurst

Abstract

The oxidation of 2-aryl tryptamines followed by a stereoselective rearrangement provides a versatile strategy for the synthesis of C3-quaternary oxindoles bearing a C3-aryl group. Treatment of optically active 2-aryl hydroxyindolenines with scandium trifluoromethanesulfonate in toluene at 110 degrees C leads to complete and stereoselective isomerization to the corresponding C3-aryl oxindoles which represent versatile intermediates for the synthesis of C3a-aryl hexahydropyrroloindoles.

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Citations

May 5, 2011·Journal of the American Chemical Society·Filip KolundzicScott J Miller
Jun 15, 2011·Journal of the American Chemical Society·Sunkyu Han, Mohammad Movassaghi
Jan 5, 2016·Journal of the American Chemical Society·Richard P LoachMohammad Movassaghi
Mar 18, 2016·ACS Medicinal Chemistry Letters·Yijun DengStephen M Condon
Jun 28, 2016·Chemistry : a European Journal·Nadège DavidChristopher J Moody
May 16, 2014·Nature·Eduardo V Mercado-MarinRichmond Sarpong
Sep 3, 2014·Organic & Biomolecular Chemistry·Lakshmana K KinthadaAlakesh Bisai
Oct 23, 2014·The Journal of Organic Chemistry·Daad SarrafJoëlle Vidal
Dec 20, 2016·Chemistry : a European Journal·Chunngai HuiJing Xu
Mar 14, 2018·Chemistry : a European Journal·Hortense LauwickMathieu Achard
Jul 6, 2012·Chemistry : a European Journal·Chepuri V Suneel KumarChepuri V Ramana
Dec 5, 2012·Angewandte Chemie·Chun-Xiang ZhuoShu-Li You
Jun 26, 2014·Angewandte Chemie·Yu SunAng Li
Jan 5, 2019·Chembiochem : a European Journal of Chemical Biology·Verrill M Norwood, Robert W Huigens
Dec 18, 2013·Chemical Communications : Chem Comm·Long HanShu-Li You
Sep 5, 2015·Chemistry : a European Journal·Weiliang ChenXiaoming Feng
Dec 29, 2020·Angewandte Chemie·Yu-Ping HeJieping Zhu
Feb 26, 2021·Organic Letters·Jiye JeonCheol-Hong Cheon
Aug 4, 2009·Organic Letters·Nicolas DuguetAndrew D Smith
Jun 16, 2011·Journal of the American Chemical Society·Xiangbing QiUttam K Tambar
Apr 2, 2013·Journal of the American Chemical Society·Madeleine E KiefferSarah E Reisman
Oct 17, 2013·The Journal of Organic Chemistry·Sunkyu HanMohammad Movassaghi
Oct 25, 2014·The Journal of Organic Chemistry·Richard P LoachMohammad Movassaghi
Jun 26, 2012·The Journal of Organic Chemistry·Marika RighiGilberto Spadoni
Sep 24, 2014·Journal of the American Chemical Society·Xin ZhangWilliam D Wulff
Jul 30, 2019·Journal of the American Chemical Society·Lucas A MorrillNeil K Garg

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