Strategies for the enantioselective synthesis of spirooxindoles

Organic & Biomolecular Chemistry
Nicolas R Ball-JonesAnnaliese K Franz

Abstract

Oxindoles and spirooxindoles are important synthetic targets that are often considered to be prevalidated with respect to their biological activity and applications for pharmaceutical lead discovery. This review features efficient strategies for the enantioselective synthesis of spirocyclic oxindoles, focusing on reports in 2010 and 2011. Although enantioselective synthesis remains an ongoing challenge, exciting recent advances in this area feature spirooxindoles with greater complexity, up to eight stereogenic centers, more practical synthetic methods, and new catalytic activation strategies. Developments in catalyst systems and reaction conditions have shown that many reactions can be optimized to control selectivity and provide access to isomeric products, which are important for biological testing. This review is organized based on two primary disconnection strategies, and then further subdivided into the type and ring size of the spirocycle that is generated. Strategies are also compared for the synthesis of non-spirocyclic 3,3'-disubstituted oxindoles.

References

Dec 14, 2001·Journal of Medicinal Chemistry·T TokunagaR Nagata
Dec 9, 2004·Journal of the American Chemical Society·Michael M-C LoStuart L Schreiber
Oct 25, 2007·Chemical Reviews·Dieter EndersAlexander Henseler
Sep 2, 2009·Organic Letters·M Paola CastaldiJohn A Porco
Sep 10, 2009·Journal of the American Chemical Society·Xiao-Hua ChenLiu-Zhu Gong
Dec 24, 2009·Angewandte Chemie·Nadine V HanhanAnnaliese K Franz
Jun 10, 2010·Chemistry : a European Journal·Pankaj Chauhan, Swapandeep Singh Chimni
Aug 24, 2010·Chemical Communications : Chem Comm·Xavier CompanyóRamon Rios
Sep 4, 2010·Science·Matthias RottmannThierry T Diagana
Sep 21, 2010·Chemistry : a European Journal·Arnaud VoituriezAngela Marinetti
Oct 14, 2010·Journal of the American Chemical Society·Yun-Lin LiuJian Zhou
Jan 27, 2011·Angewandte Chemie·Michael MastalerzOliver Presly
Feb 11, 2011·Chemistry : a European Journal·Fabio PesciaioliGiorgio Bencivenni
Jul 29, 2011·Organic & Biomolecular Chemistry·Jan Schönhaber, Thomas J J Müller
Aug 11, 2011·Chemical Communications : Chem Comm·Li-Hui SunSong Ye
Aug 17, 2011·Journal of the American Chemical Society·Yankai LiuPaolo Melchiorre

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Citations

Jun 5, 2013·ACS Combinatorial Science·Matthew G LaPortePaul E Floreancig
Jul 25, 2013·The Journal of Organic Chemistry·Artur NooleTõnis Kanger
Jul 25, 2013·Organic Letters·Maxime GicquelAngela Marinetti
Jun 15, 2013·Beilstein Journal of Organic Chemistry·Qin Fu, Chao-Guo Yan
Oct 23, 2014·The Journal of Organic Chemistry·Daad SarrafJoëlle Vidal
Mar 13, 2014·Organic Letters·Sergei ŽariTõnis Kanger
Sep 4, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Fernando Auria-LunaRaquel P Herrera
Feb 7, 2015·The Journal of Organic Chemistry·Xueqin LiYufen Zhao
Nov 6, 2015·The Journal of Organic Chemistry·Meagan E HinzeChad A Lewis
Jul 6, 2014·European Journal of Medicinal Chemistry·Bin YuHong-Min Liu
Jul 8, 2015·Journal of the American Chemical Society·Peng-Fei ZhengYing-Chun Chen
Sep 15, 2016·ACS Infectious Diseases·Na YeJia Zhou

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