A versatile method for the synthesis of 3-alkoxycarbonyl beta-lactam derivatives.
[reaction: see text] Ketene-imine cycloaddition reactions (the Staudinger reaction) of ethoxycarbonyl(phenylthio)ketene with various imines and subsequent desulfurization reactions were employed to synthesize 3-ethoxycarbonyl beta-lactam derivatives. The results indicate that the current approach provides a convenient, mild, and versatile method for synthesizing a variety of 3-alkoxycarbonyl trans-beta-lactam derivatives with good to excellent yields and diastereoselectivities.
Jiao
Lei
L
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China.
Zhang
Qianfeng
Q
Liang
Yong
Y
Zhang
Shiwei
S
Xu
Jiaxi
J
D000478:Alkylation; D005030:Ethylenes; D007202:Indicators and Reagents; D007659:Ketones; D008958:Models, Molecular; D008968:Molecular Conformation; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry*
D005030:Ethylenes; D007202:Indicators and Reagents; D007659:Ketones; D047090:beta-Lactams; C008223:ketene