Phosphite Catalyzed C-H Allylation of Azaarenes via an Enantioselective [2,3]-Aza-Wittig Rearrangement

Angewandte Chemie
Abdul MotalebPradip Maity

Abstract

A phosphite mediated [2,3]-aza-Wittig rearrangement has been developed for the regio- and enantioselective allylic alkylation of six-membered hetero-aromatic compounds (azaarenes). The nucleophilic phosphite adduct of N-allyl salts undergoes a stereoselective base mediated aza-Wittig rearrangement and dissociation of the chiral phosphite for overall C-H functionalization of azaarenes. This method provides efficient access to tertiary and quaternary chiral centers in isoquinoline, quinoline, and pyridine systems, tolerating a broad variety of substituents on both allyl part and azaarenes. Catalysis with chiral phosphites is also demonstrated with synthetically useful yields and enantioselectivities.

References

Jan 10, 2001·The Journal of Organic Chemistry·J C AndersonM E Swarbrick
Nov 15, 1996·The Journal of Organic Chemistry·Jens ÅhmanPeter Somfai
Mar 11, 2004·Chemical Reviews·Bruce E MaryanoffCynthia A Maryanoff
Mar 12, 2004·Journal of the American Chemical Society·Xin LinghuJeffrey S Johnson
Feb 24, 2006·Journal of the American Chemical Society·Mary R NahmJeffrey S Johnson
Apr 11, 2006·Organic & Biomolecular Chemistry·Ben ClarkJennifer H Gill
Jul 14, 2006·Chemical Reviews·Vittorio FarinaJinhua J Song
Jan 18, 2007·Chemical Society Reviews·Giorgio Chelucci
Oct 12, 2007·Journal of the American Chemical Society·Mary R GarrettJeffrey S Johnson
Feb 6, 2008·Natural Product Reports·Joseph P Michael
Aug 27, 2009·Organic Letters·Ethan L Fisher, Tristan H Lambert
Jan 13, 2012·Current Topics in Medicinal Chemistry·Linus ChiangTim Storr
Nov 10, 2013·Beilstein Journal of Organic Chemistry·Marcus Baumann, Ian R Baxendale
Aug 19, 2014·Journal of the American Chemical Society·Guoyong SongZhaomin Hou
Oct 14, 2014·Journal of the American Chemical Society·Ren-Qi XuShu-Li You
Jul 24, 2015·Nature·Yongwei WuLi Deng
Aug 22, 2015·Journal of the American Chemical Society·Josep LlaveriaVarinder K Aggarwal
Dec 24, 2015·Angewandte Chemie·Santanu PandaJoseph M Ready
Apr 21, 2016·Angewandte Chemie·Cyril PiemontesiJieping Zhu
Sep 30, 2016·Chemical Reviews·Maria ChrzanowskaMaria D Rozwadowska
Apr 27, 2017·Chemical Reviews·Kei MurakamiKenichiro Itami
Jul 6, 2017·Journal of the American Chemical Society·Patrick S Fier
Jan 11, 2018·Journal of the American Chemical Society·Xingyu JiangJohn F Hartwig
Apr 4, 2018·Chemical Communications : Chem Comm·Giulio BertuzziMariafrancesca Fochi
Apr 7, 2018·Science·Rupert S J ProctorRobert J Phipps
May 25, 2018·Journal of the American Chemical Society·Naofumi HaraYoshiaki Nakao
Jun 28, 2018·Organic & Biomolecular Chemistry·Abdul MotalebPradip Maity
Jul 13, 2018·The Journal of Organic Chemistry·Viktor BarátRoderick W Bates
Sep 27, 2018·Organic Letters·Xiangyuan LiuZhiyong Jiang

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