Diastereoselective synthesis of a bicyclic β-lactam with penicillin G-like spectrum of activity by carbonylation of an acyclic diaminocarbene

Tim Schulz; Christian Färber; Michael Leibold; Clemens Bruhn; Pascal Prochnow; Julia E. Bandow; Tanja Schneider; Timo Porsch; Max C. Holthausen; Ulrich Siemeling

doi:10.1039/C3CC48538B

Diastereoselective synthesis of a bicyclic β-lactam with penicillin G-like spectrum of activity by carbonylation of an acyclic diaminocarbene†

Tim Schulz,^a Christian Färber,^a Michael Leibold,^a Clemens Bruhn,^a Pascal Prochnow,^b Julia E. Bandow,^b Tanja Schneider,^c Timo Porsch,^d Max C. Holthausen*^d and Ulrich Siemeling*^a

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^a Institute of Chemistry, University of Kassel, Heinrich-Plett-Str. 40, D-34132 Kassel, Germany
E-mail: siemeling@uni-kassel.de

^b Biology of Microorganisms, Ruhr University Bochum, Universitätsstr. 150, D-44801 Bochum, Germany

^c Pharmaceutical Microbiology, University of Bonn, Meckenheimer Allee 168, D-53115 Bonn, Germany

^d Institut für Anorganische und Analytische Chemie, Johann Wolfgang Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, D-60438 Frankfurt am Main, Germany
E-mail: max.holthausen@chemie.uni-frankfurt.de

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.

Chemical Communications

Diastereoselective synthesis of a bicyclic β-lactam with penicillin G-like spectrum of activity by carbonylation of an acyclic diaminocarbene†

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Diastereoselective synthesis of a bicyclic β-lactam with penicillin G-like spectrum of activity by carbonylation of an acyclic diaminocarbene

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