Diastereoselective synthesis of carbapenams via Kinugasa reaction.
A facile approach to carbapenams via Kinugasa reaction between terminal copper acetylides and nonracemic cyclic nitrones derived from malic and tartaric acid is reported. The stereochemical preferences observed in these reactions are explained. The reaction provides an entry to the carbapenams basic skeleton.
Stecko
Sebastian
S
Institute of Organic Chemistry of Polish Academy of Sciences Kasprzaka 44/52, 01-224 Warsaw, Poland.
Mames
Adam
A
Furman
Bartłomiej
B
Chmielewski
Marek
M
D000480:Alkynes / Q000737:chemistry*; D015780:Carbapenems / Q000138:chemical synthesis* / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D003497:Cyclic N-Oxides / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000480:Alkynes; D015780:Carbapenems; D003497:Cyclic N-Oxides; D007454:Iodides; D003300:Copper; C073870:cuprous iodide