Diastereoselective synthesis of a bicyclic β-lactam with penicillin G-like spectrum of activity by carbonylation of an acyclic diaminocarbene.
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.
Institute of Chemistry, University of Kassel, Heinrich-Plett-Str. 40, D-34132 Kassel, Germany. siemeling@uni-kassel.de.
Tim
T
Schulz
Christian
C
Färber
Michael
M
Leibold
Clemens
C
Bruhn
Pascal
P
Prochnow
Julia E
JE
Bandow
Tanja
T
Schneider
Timo
T
Porsch
Max C
MC
Holthausen
Ulrich
U
Siemeling
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002248:Carbon Monoxide / Q000737:chemistry; D004148:Dioxolanes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010400:Penicillin G / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism; D047090:beta-Lactams / Q000737:chemistry*
D000480:Alkynes; D001643:Bridged Bicyclo Compounds; D004148:Dioxolanes; C504703:aminocarbene; D047090:beta-Lactams; D002248:Carbon Monoxide; D010400:Penicillin G