Intermolecular Addition of Amines to an N-Tosyloxy β-Lactam¹

Methodology for Monobactam Diversification: Syntheses and Studies of 4-Thiomethyl Substituted β-Lactams with Activity against Gram-Negative Bacteria, Including Carbapenemase Producing Acinetobacter baumannii

“…The target molecules, 13 , with various acyl and R groups, could be obtained from 14 by a now-standard sulfonation reaction. Introduction of acylamino side chains at the C(3) position would be preceded by azide reduction of compounds 15 , which would be formed by direct reaction of N -tosyloxy β-lactams, 16 , with azide as previously described by our group. − Finally β-lactams 16 could be obtained by functional group manipulation of azetidinone 12 .…”

The Chemistry of Vicinal Diamines

“…[172,173] A significant example has been reported by Evans and Sjogren (Scheme 96): [174] the Staudinger reaction of the ketene derived from a chiral, enantiomerically pure oxazolidylacetyl chloride 397 with imines 396 led with very good diastereoselection to the corresponding cis-b-lactams 398. The oxazolidinone ring can then be cleaved to generate an amino group.…”

A general and versatile synthesis of 3‐phenylthio β‐lactams as lead molecules for 3‐methyl‐2‐azetidinones

“…Transformation at the C -3 carbon of -lactams leading to the formation of diverse molecules involving anionic and cationic -lactam equivalents a and b respectively ( Figure 2) are an important area of research [24,25]. The potential of the cationic -lactam equivalent of type b has been explored by many groups [26][27][28] for the preparation of different -lactam synthons. However, the chemistry involving the anionic -lactam equivalents has not been extensively studied.…”