Preference of beta-lactam formation in Cu(I)-catalyzed intramolecular coupling of amides with vinyl bromides

Organic Letters
Qiwu Zhao, Chaozhong Li

Abstract

A general and highly efficient synthesis of 4-alkylidene-2-azetidinones was achieved by the Cu(I)-catalyzed intramolecular C-N coupling of amides with vinyl bromides. This 4-exo ring closure was found to be fundamentally preferred over other modes (5-exo, 6-exo, and 6-endo) of cyclization under copper catalysis. Tandem C-N bond formation was then successfully developed to allow the convenient generation of medium-sized lactams.

References

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Citations

Nov 14, 2013·Organic Preparations and Procedures International·Hao Lin, Dianqing Sun
Nov 25, 2011·Chemistry : a European Journal·Rebecca L GreenawayEdward A Anderson
Sep 22, 2009·The Journal of Organic Chemistry·Santos FusteroGerald B Hammond
Jun 9, 2011·Organic Letters·Liyan SongChaozhong Li
Nov 21, 2014·The Journal of Organic Chemistry·Lin ZhuChaozhong Li
Feb 22, 2014·Chemical Reviews·Cody Ross Pitts, Thomas Lectka
Sep 16, 2011·Organic Letters·Deqian SunChaozhong Li
Dec 17, 2016·The Journal of Organic Chemistry·Gerardo M TorresBruce A Arndtsen
Aug 16, 2014·The Journal of Organic Chemistry·Qian LiaoChanjuan Xi

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