Abstract
Diisopropylamino-cis-2,6-dimethylpiperidinocarbene reacts regio- and diastereoselectively with CO to afford a bicyclic β-lactam with 100% atom efficiency, whose spectrum of activity resembles that of penicillin G or amoxicillin.
Highlights
Diastereoselective synthesis of a bicyclic b-lactam with penicillin G-like spectrum of activity by carbonylation of an acyclic diaminocarbene†
Diisopropylamino-cis-2,6-dimethylpiperidinocarbene reacts regioand diastereoselectively with CO to afford a bicyclic b-lactam with 100% atom efficiency, whose spectrum of activity resembles that of penicillin G or amoxicillin
As a first milestone of a systematic study to probe the limitations of this new synthetic method, we have shown that b-lactam formation requires very bulky acyclic diaminocarbenes (ADACs).8b We here address the question whether this reaction can be applied to the synthesis of bicyclic b-lactams, using bulky ADACs with cyclic amino groups
Summary
Diastereoselective synthesis of a bicyclic b-lactam with penicillin G-like spectrum of activity by carbonylation of an acyclic diaminocarbene†. Diisopropylamino-cis-2,6-dimethylpiperidinocarbene reacts regioand diastereoselectively with CO to afford a bicyclic b-lactam with 100% atom efficiency, whose spectrum of activity resembles that of penicillin G or amoxicillin.
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