Β‐Lactam Synthesis through Diodomethane Addition to Amide Dianions. Issue 40 (24th August 2017)

• Record Type: Journal Article
• Authors: Zidan, Alaa; Garrec, Julian; Cordier, Marie; El‐Naggar, Abeer M.; Abd El‐Sattar, Nour E. A.; Ali, Ali Khalil; Hassan, Mohamed Ali; El Kaim, Laurent
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 40(2017)
• Page Start: 12179
• Page End: 12183
• Publication Date: 2017-08-24
• Subjects: amides -- β-lactams -- diiodomethane -- diversity-oriented synthesis -- Ugi reactions; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201706315
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: We present a novel route for the quick and easy synthesis of a broad range of β‐lactams. The synthesis involves a [3+1] cyclization of amide dianions with diiodomethane. In contrast to the seminal work of Hirai et al. from 1979, the reaction proved to be a general and efficient approach towards azetidinones. The ease of the process was confirmed by DFT calculations and its power demonstrated by a diversity‐oriented synthesis of β‐lactams with four points of diversity determined by the choice of Ugi adducts as starting materials. Abstract : Old dog new tricks : A facile synthesis of a broad range of β‐lactams through [3+1] cyclization of amide dianions with diiodomethane was developed. In contrast to the seminal work of Hirai et al. from 1979, the reaction proved to be a general and efficient approach towards azetidinones. The utility of the process was demonstrated by a diversity‐oriented synthesis of β‐lactams with four points of diversity determined by the choice of Ugi adducts as starting materials.