Ruthenium-catalyzed isomerization of oxa/azabicyclic alkenes: an expedient route for the synthesis of 1,2-naphthalene oxides and imines

Journal of the American Chemical Society
Karine Villeneuve, William Tam

Abstract

1,2-Naphthalene oxides and imines can be rapidly accessed through a ruthenium-catalyzed isomerization of readily available 7-oxa/azabenzonorbornadienes. These mild reaction conditions were found to be tolerant to various functional groups and the isomerization is highly regioselective.

References

Jun 30, 2001·The Journal of Organic Chemistry·A M CastañoA M Echavarren
Jul 13, 2001·Journal of the American Chemical Society·D E KaelinS F Martin
Oct 25, 2001·The Journal of Organic Chemistry·Chiou-Chii FengChien-Hong Cheng
Oct 23, 2003·Journal of the American Chemical Society·David E KaelinStephen F Martin
Apr 7, 2004·Proceedings of the National Academy of Sciences of the United States of America·Mark Lautens, Keith Fagnou
Nov 19, 2004·Organic Letters·Karine VilleneuveWilliam Tam
Aug 12, 2005·Organic Letters·Nicole RiddellWilliam Tam

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Citations

Nov 6, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Huayi SuoJianquan Kan
Dec 4, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wen YangDingqiao Yang
Jun 19, 2013·Organic & Biomolecular Chemistry·Dingqiao YangChunrong Li
Oct 31, 2013·Organic & Biomolecular Chemistry·Maxim V PonomarenkoGerd-Volker Röschenthaler
Nov 11, 2016·Beilstein Journal of Organic Chemistry·Katrina TaitWilliam Tam
Feb 20, 2014·Organic & Biomolecular Chemistry·Dingqiao Yang, Ni Liang
Apr 16, 2011·Angewandte Chemie·Philipp BissingerThomas Kupfer
Jan 28, 2020·Current Organic Synthesis·Rebecca BoutinWilliam Tam
Dec 12, 2012·Organic & Biomolecular Chemistry·Jun HuAlbert S C Chan
May 25, 2006·Journal of the American Chemical Society·Yong-hwan ChoMark Lautens
Sep 4, 2009·The Journal of Organic Chemistry·Melissa BallantineWilliam Tam
Sep 8, 2009·The Journal of Organic Chemistry·Ben P MachinWilliam Tam
Oct 9, 2012·The Journal of Organic Chemistry·Hanchao Cheng, Dingqiao Yang
Jun 14, 2019·The Journal of Organic Chemistry·Jarvis Hill, William Tam
Mar 10, 2015·The Journal of Organic Chemistry·Matthew J MoschittoChad A Lewis
Sep 13, 2019·The Journal of Organic Chemistry·Donghan ChenDingqiao Yang
Aug 31, 2019·The Journal of Organic Chemistry·Shuqi ChenDingqiao Yang
Oct 20, 2006·Organic Letters·Dong ZhangMatthias Selke
Aug 19, 2007·The Journal of Organic Chemistry·Ryan R Burton, William Tam
Jul 31, 2007·Organic Letters·Ryan R Burton, William Tam

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