Enantioselective Conia-Ene-Type Cyclizations of Alkynyl Ketones through Cooperative Action of B(C6 F5 )3 , N-Alkylamine and a Zn-Based Catalyst

Journal of the American Chemical Society
Min CaoMasayuki Wasa

Abstract

An efficient and highly enantioselective Conia-ene-type process has been developed. Reactions are catalyzed by a combination of B(C6F5)3, an N-alkylamine and a BOX-ZnI2 complex. Specifically, through cooperative action of B(C6F5)3 and amine, ketones with poorly acidic α-C-H bonds can be converted in situ to the corresponding enolates. Subsequent enantioselective cyclization involving a BOX-ZnI2-activated alkyne leads to the formation of various cyclopentenes in up to 99% yield and 99:1 er.

References

Mar 17, 2005·Angewandte Chemie·Hisashi Yamamoto, Kentaro Futatsugi
Dec 8, 2005·Journal of the American Chemical Society·Britton K Corkey, F Dean Toste
Feb 20, 2007·Journal of the American Chemical Society·Britton K Corkey, F Dean Toste
May 26, 2007·Angewandte Chemie·Takashi Ooi, Keiji Maruoka
Dec 13, 2007·Chemical Reviews·Takuya Hashimoto, Keiji Maruoka
Apr 12, 2008·Accounts of Chemical Research·Daniel H PaullThomas Lectka
May 8, 2009·Chemical Society Reviews·Zhiguo Zhang, Peter R Schreiner
Jun 17, 2009·Journal of the American Chemical Society·Ting YangDarren J Dixon
Jun 8, 2011·Angewandte Chemie·Akinobu MatsuzawaMasakatsu Shibasaki
Nov 15, 2011·Chemical Reviews·Giovanni DesimoniKarl Anker Jørgensen
Feb 3, 2012·Journal of the American Chemical Society·Jean-François BrazeauF Dean Toste
May 19, 2012·Organic Letters·Xiaozu Liu, Chi-Sing Lee
Jul 25, 2012·Nature Chemistry·Robert J PhippsF Dean Toste
Nov 2, 2012·Topics in Current Chemistry·Andrew E Ashley, Dermot O'Hare
Nov 20, 2012·Angewandte Chemie·Nikolas Huwyler, Erick M Carreira
Nov 30, 2012·Angewandte Chemie·Katrien Brak, Eric N Jacobsen
Jan 2, 2013·Topics in Current Chemistry·Douglas W Stephan, Gerhard Erker
Sep 17, 2013·Chemistry : a European Journal·Peter PersichAlois Fürstner
Dec 21, 2013·Journal of the American Chemical Society·Max M HansmannDouglas W Stephan
Jan 16, 2014·Chemical Communications : Chem Comm·Xiaochun XiongAng Li
Sep 13, 2014·Journal of the American Chemical Society·Subrata Shaw, James D White
Feb 5, 2015·Accounts of Chemical Research·Barry M Trost, Mark J Bartlett
Feb 14, 2015·Chemical Society Reviews·Martin OestreichJens Mohr
May 15, 2015·Angewandte Chemie·Douglas W Stephan, Gerhard Erker
Jun 3, 2015·Chemical Society Reviews·Daniel HackDieter Enders
Jul 28, 2015·Journal of the American Chemical Society·Douglas W Stephan
Oct 22, 2016·Angewandte Chemie·Jessica Z ChanMasayuki Wasa
Dec 13, 2016·Science·Douglas W Stephan
Dec 17, 2016·Journal of the American Chemical Society·Ming ShangMasayuki Wasa
Mar 23, 2017·Chemical Communications : Chem Comm·M BlümelD Enders
Mar 31, 2017·Nature·Andrew J NeelF Dean Toste
Jul 4, 2017·The Journal of Organic Chemistry·Felix W W Hartrampf, Dirk Trauner
Dec 12, 2017·Journal of the American Chemical Society·Qinda YeScott A Snyder

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Citations

Apr 8, 2020·Advanced Synthesis & Catalysis·Yejin ChangMasayuki Wasa
Dec 17, 2020·Chemical Society Reviews·Yuanhong MaZhaomin Hou
Jan 23, 2021·Organic & Biomolecular Chemistry·Gautam KumarIndranil Chatterjee
Feb 12, 2021·Journal of the American Chemical Society·Jun-Jie TianXiao-Chen Wang
Apr 17, 2021·Chemistry : a European Journal·Masatoshi ShibuyaYoshihiko Yamamoto
Sep 5, 2019·Journal of the American Chemical Society·Yejin ChangMasayuki Wasa
Jul 10, 2020·The Journal of Organic Chemistry·Geoffrey SchwertzJanine Cossy
Jan 7, 2022·Chemical Communications : Chem Comm·Bao YuGeoffroy Sorin

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