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β‐Lactam Synthesis through Diodomethane Addition to Amide Dianions
Author(s) -
Zidan Alaa,
Garrec Julian,
Cordier Marie,
ElNaggar Abeer M.,
Abd ElSattar Nour E. A.,
Ali Ali Khalil,
Hassan Mohamed Ali,
El Kaim Laurent
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201706315
Subject(s) - diiodomethane , amide , adduct , ugi reaction , chemistry , lactam , combinatorial chemistry , stereochemistry , organic chemistry , isocyanide , surface energy
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.