Organocatalytic tandem reaction to construct six-membered spirocyclic oxindoles with multiple chiral centres through a formal [2+2+2] annulation

Chemistry : a European Journal
Kun JiangYing-Chun Chen

Abstract

An efficient tandem reaction for the asymmetric synthesis of six-membered spirocyclic oxindoles has been successfully developed through a formal [2+2+2] annulation strategy. The amine-catalysed stereoselective Michael addition of aliphatic aldehydes to electron-deficient olefinic oxindole motifs gave chiral C3 components, which were further combined with diverse electrophiles (activated olefins or imines) to afford spirocyclic oxindoles with versatile molecular complexity (up to six contiguous stereogenic centres, high diastereo- and enantioselectivities).

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Citations

Jul 1, 2011·The Journal of Organic Chemistry·Patrick G McGarraughStacey E Brenner-Moyer
Oct 22, 2010·Organic Letters·Chunliang LuPaul E Floreancig
Sep 29, 2012·Beilstein Journal of Organic Chemistry·Jin-Sheng YuJian Zhou
Mar 12, 2016·Chemical Communications : Chem Comm·Zhenghua LiErik V Van der Eycken
Aug 15, 2012·Chemistry : a European Journal·Hongxin LiuJun Jiang
Dec 7, 2013·Chemistry : a European Journal·Sébastien GoudedrancheJean Rodriguez
Aug 24, 2010·Chemical Communications : Chem Comm·Xavier CompanyóRamon Rios
Sep 21, 2010·Chemistry : a European Journal·Arnaud VoituriezAngela Marinetti
Dec 17, 2011·Chemical Science·Keith J BartelsonLi Deng
Jan 13, 2012·Organic & Biomolecular Chemistry·Andrea MazzantiRamon Rios
Jan 24, 2012·Chemical Communications : Chem Comm·Xin HuangYing-Chun Chen
Mar 21, 2012·Organic & Biomolecular Chemistry·Feng ZhouJian Zhou
May 15, 2012·Organic & Biomolecular Chemistry·Nicolas R Ball-JonesAnnaliese K Franz
Oct 12, 2013·Chemistry : a European Journal·Ulf Scheffler, Rainer Mahrwald

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