Synthesis of Chiral Spiro-Aziridine Oxindoles via Aza-Corey-Chaykovsky Reaction of Isatin Derived N-tert-Butanesulfinyl Ketimines

Organic Letters
Saumen HajraDhiraj Das

Abstract

A general and direct strategy for the synthesis of chiral spiro-aziridine oxindoles has been developed via an aza-Corey-Chaykovsky reaction of isatin-derived N-tert-butanesulfinyl ketimines with excellent selectivity (dr = 98:2 to >99:1). The method is explored for the synthesis of chiral 3-substituted spiro-aziridine oxindoles with high (2S,3S)-selectivity over (2S,3R).

References

Oct 3, 2002·Chemical Society Reviews·J B Sweeney
Nov 20, 2002·Accounts of Chemical Research·Jonathan A EllmanTony P Tang
Jul 2, 2004·Organic Letters·Daniel MortonRobert A Stockman
Apr 20, 2006·Chemical Communications : Chem Comm·Daniel MortonRobert A Stockman
Nov 18, 2006·The Journal of Organic Chemistry·Franklin A Davis
Mar 31, 2007·Organic Letters·Verena SchulzJean-François Brière
May 10, 2007·Chemical Reviews·Girija S SinghNorbert De Kimpe
Jan 29, 2009·Angewandte Chemie·Christoph Schneider
May 8, 2009·Chemical Society Reviews·Franck FerreiraAlejandro Pérez-Luna
May 15, 2009·The Journal of Organic Chemistry·Giordano LesmaAlessandra Silvani
Jun 23, 2009·European Journal of Medicinal Chemistry·Fyaz M D IsmailValery M Dembitsky
Apr 28, 2010·Chemical Reviews·MaryAnn T RobakJonathan A Ellman
Feb 16, 2011·Chemical Communications : Chem Comm·Saumen Hajra, Sukanta Bar
Sep 7, 2011·Chemical Society Reviews·Sonja StankovićHyun-Joon Ha
Oct 7, 2011·Chemical Society Reviews·Ramon Rios
Sep 7, 2012·Chemical Reviews·Girija S Singh, Zelalem Y Desta
Jan 11, 2013·Chemical Communications : Chem Comm·Jianhao LiYungui Peng
Jun 15, 2013·Beilstein Journal of Organic Chemistry·Qin Fu, Chao-Guo Yan
Apr 16, 2014·The Journal of Organic Chemistry·Amina BoucherifWen-Jing Xiao
Apr 30, 2014·Chemical Reviews·Gert CallebautSven Mangelinckx
May 16, 2014·Chemical Reviews·Leonardo DegennaroRenzo Luisi

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Citations

Apr 18, 2018·Organic & Biomolecular Chemistry·Jasneet Kaur, Swapandeep Singh Chimni
Oct 31, 2017·Organic & Biomolecular Chemistry·Saumen HajraAtanu Hazra
May 18, 2018·Chemical Communications : Chem Comm·Guang-Jian Mei, Feng Shi
Oct 13, 2020·Organic & Biomolecular Chemistry·Akash P SaklaNagula Shankaraiah

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