Redox tuning of a direct asymmetric aldol reaction

Angewandte Chemie
Qiying ZhangYangjie Wu

Abstract

Presented herein is a redox tuning strategy for asymmetric aminocatalysis with a designed chiral ferrocenophane. Under redox control, the ferrocenophane catalyst efficiently catalyzes the asymmetric aldol reaction at room temperature with excellent yield and good stereoselectivity. Moreover, the redox-active ferrocene moiety also served as phase-tag to facilitate catalyst recovery and reuse. The catalyst can be reused for five cycles without much loss of activity. Ferrocenium of the oxidized ferrocenophane was proposed to serve as Lewis acidic site, thus accounting for the stereo control.

References

Aug 17, 2004·Science·Alan B Northrup, David W C MacMillan
Sep 30, 2004·Angewandte Chemie·Peter I Dalko, Lionel Moisan
Oct 27, 2005·Angewandte Chemie·Marcus Süssner, Herbert Plenio
Dec 31, 2005·Angewandte Chemie·Yujiro HayashiMitsuru Shoji
Jan 19, 2006·Journal of the American Chemical Society·Nobuyuki MaseCarlos F Barbas
Jan 26, 2006·Journal of the American Chemical Society·Susumu MitsumoriCarlos F Barbas
Jun 8, 2006·Journal of the American Chemical Society·Charlotte K A GregsonAndrew J P White
Nov 4, 2006·Chemical Communications : Chem Comm·Masahiro FujiwaraHiroyoshi Ohue
Nov 23, 2006·Angewandte Chemie·Ramón Gómez ArrayásJuan Carlos Carretero
Jan 1, 2008·Journal of the American Chemical Society·Mark R RingenbergThomas B Rauchfuss
Apr 9, 2008·Organic Letters·Sanzhong LuoJin-Pei Cheng
Jul 31, 2008·Angewandte Chemie·Paolo MelchiorreGiuseppe Bartoli
Nov 4, 2009·The Journal of Organic Chemistry·Sanzhong LuoJin-Pei Cheng
Mar 20, 2010·Chemistry : a European Journal·Sanzhong LuoJin-Pei Cheng
Jun 22, 2010·Journal of the American Chemical Society·Andrew G TennysonChristopher W Bielawski
Apr 2, 2011·Science·Andrew J D MagenauKrzysztof Matyjaszewski
May 25, 2011·Journal of the American Chemical Society·Erin M BroderickPaula L Diaconescu
May 4, 2012·Journal of the American Chemical Society·Shahab MortezaeiJames W Canary
Sep 15, 2012·Chemical Society Reviews·Oana R Luca, Robert H Crabtree
Sep 22, 2012·Angewandte Chemie·Vijayendran K K PraneethThomas R Ward
Nov 21, 2012·Angewandte Chemie·Frank A LeibfarthCraig J Hawker
May 8, 2013·Chemistry : a European Journal·Diego PetruzzielloPier Giorgio Cozzi
Jul 16, 2013·Chemistry : a European Journal·Kuppuswamy ArumugamChristopher W Bielawski
Oct 1, 2013·Journal of the American Chemical Society·Ashley B BiernesserJeffery A Byers
Mar 19, 2014·Chemical Communications : Chem Comm·Yongming DengHong Wang
Mar 22, 2014·Journal of the American Chemical Society·Victor BlancoAlina L Nussbaumer
Jul 26, 2014·Journal of the American Chemical Society·Xinke WangPaula L Diaconescu
Nov 22, 2014·Angewandte Chemie·Paul NeumannEvamarie Hey-Hawkins

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Citations

May 13, 2015·Chemical Society Reviews·Victor BlancoVanesa Marcos
Apr 12, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Alan A WilesGraeme Cooke
Oct 25, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Max RoemerGeorge A Koutsantonis
May 31, 2018·Chemical Society Reviews·Yasuhiro YamashitaShū Kobayashi
Jan 27, 2019·Chemical Communications : Chem Comm·Yan LiLaurent Bouteiller
Nov 26, 2019·Topics in Current Chemistry·Pier Giorgio CozziGiacomo Rodeghiero
Oct 8, 2016·Chemistry : a European Journal·Matea VlatkovićBen L Feringa

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