M. Behzadi, K. Saidi, M. Islami
2015
Citations
0
Influential Citations
14
Citations
Journal
Journal of Chemical Sciences
Abstract
Abstract3-Phenyl-2-(1-H-pyrrol-1-yl) propanoic acid has been used as a ketene source in synthesizing of monocyclic-2-azetidinones. Hindrance in ketene and imines successfully controlled the diastereoselectivity of the reaction. For example, in some cases only one isomer was achieved. By using Mukaiyama reagent, the leaving group in acid was activated and the by-products were separated by simple aqueous work-up. DFT calculation indicated that the benzyl-N-pyrrolylketene has nonconjugated structure and the pyrrolyl ring is perpendicular to the ketene plane in both the twisted and planar structures. Graphical Abstract3-Phenyl-2-(1-H-pyrrol-1-yl) propanoic acid as a ketene source has been used in synthesizing of monocyclic-2-azetidinones. Hindrance in ketene and imines successfully controlled the diastereoselectivity. DFT calculation indicated that benzyl-N-pyrrolylketene has unconjugated structure and the pyrrolyl ring is perpendicular to the ketene plane in both twisted and planner structures.