Construction of the Benzomesembrine Skeleton: Palladium(0)-Catalyzed Intermolecular Arylative Dearomatization of α-Naphthols and Subsequent Aza-Michael Reaction

Angewandte Chemie
Ren-Qi XuShu-Li You

Abstract

A novel palladium(0)-catalyzed intermolecular arylative dearomatization of α-naphthols and subsequent aza-Michael reaction is described. Two adjacent stereocenters were constructed efficiently through consecutive arylative dearomatization and Michael addition reactions. By utilizing this method, structurally diverse benzomesembrine derivatives were synthesized with excellent yields and chemoselectivity. The benzomesembrine products were shown to undergo versatile functional-group transformations.

References

Dec 26, 2001·Chemical Reviews·A R PapeE P Kündig
May 23, 2002·Journal of the American Chemical Society·Jingjun Yin, Stephen L Buchwald
Aug 28, 2002·Natural Product Reports·Zhong JinRunqiu Huang
Oct 1, 1957·Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft·K BODENDORF, W KRIEGER
Jul 27, 2007·Natural Product Reports·Zhong Jin
Apr 9, 2008·Angewandte Chemie·Toshifumi DohiYasuyuki Kita
Jul 16, 2008·Accounts of Chemical Research·Ruben Martin, Stephen L Buchwald
Mar 31, 2009·Journal of the American Chemical Society·Min ZhangYong Qin
Apr 25, 2009·Journal of the American Chemical Society·Jorge García-FortanetStephen L Buchwald
Aug 5, 2009·Chemical Communications : Chem Comm·Robin B BedfordRosalind F Sankey
Sep 4, 2010·Journal of the American Chemical Society·Zhiwei ZuoDawei Ma
Feb 18, 2011·Chemical Communications : Chem Comm·Robin B BedfordRosalind F Sankey
Apr 21, 2011·Angewandte Chemie·Stéphane P Roche, John A Porco
May 27, 2011·Journal of the American Chemical Society·Sophie RousseauxStephen L Buchwald
Oct 19, 2011·Angewandte Chemie·Zhiwei Zuo, Dawei Ma
Jan 17, 2012·Journal of the American Chemical Society·Axel KirsteSiegfried R Waldvogel
May 24, 2012·Journal of the American Chemical Society·Weiwei ZiDawei Ma
Dec 5, 2012·Angewandte Chemie·Chun-Xiang ZhuoShu-Li You
Jan 22, 2013·Journal of the American Chemical Society·Robert J Phipps, F Dean Toste
Aug 21, 2013·Chemical Communications : Chem Comm·Ke-Jia WuShu-Li You
Nov 8, 2013·Journal of the American Chemical Society·Jiang NanYaoyu Wang
Feb 1, 2014·Angewandte Chemie·Mingxing TengDawei Ma
Mar 8, 2014·Beilstein Journal of Organic Chemistry·Shinichi YamabeShigeyoshi Sakaki
Jun 19, 2014·Accounts of Chemical Research·Chun-Xiang ZhuoShu-Li You
Oct 14, 2014·Journal of the American Chemical Society·Ren-Qi XuShu-Li You
Feb 24, 2015·Organic & Biomolecular Chemistry·Mrinal Kanti DasAlakesh Bisai
Apr 8, 2015·Journal of the American Chemical Society·Chong ShenYi-Xia Jia
Apr 9, 2015·Journal of the American Chemical Society·Jun ZhengShu-Li You
Jan 8, 2016·Organic & Biomolecular Chemistry·Wangsheng SunRui Wang

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Citations

Dec 2, 2017·Chemistry : a European Journal·Juzeng AnMarco Bandini
May 28, 2020·Organic & Biomolecular Chemistry·Zhuo Wang
Jun 22, 2017·Chemical Communications : Chem Comm·Ren-Qi XuShu-Li You
Apr 23, 2021·Journal of the American Chemical Society·Euijae LeeSukbok Chang
Aug 12, 2021·Organic & Biomolecular Chemistry·Hong-Wei Chen, Qin-Hua Song
Nov 13, 2018·Organic Letters·Juzeng AnMarco Bandini
Sep 27, 2018·Journal of the American Chemical Society·Xiang LiYi-Xia Jia

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