Premium
Base‐Mediated Generation of Ketenimines from Ynamides: Direct Access to Azetidinimines by an Imino‐Staudinger Synthesis
Author(s) -
Romero Eugénie,
Minard Corinne,
Benchekroun Mohamed,
Ventre Sandrine,
Retailleau Pascal,
Dodd Robert H.,
Cariou Kevin
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702545
Subject(s) - cycloaddition , chemistry , combinatorial chemistry , staudinger reaction , stereochemistry , organic chemistry , catalysis
Ynamides were used as precursors for the in situ generation of highly reactive ketenimines that could be trapped with imines in a [2+2] cycloaddition. This imino‐Staudinger synthesis led to a variety of imino‐analogs of β‐lactams, namely azetidinimines (20 examples), that could be further functionalized through a broad range of transformations.