P(NMe<sub>2</sub>)<sub>3</sub> mediated cyclopropanation of α-methylene-β-lactams for rapid syntheses of spirocyclopropyl β-lactams
Si-Qin Luo, Wei Liu, Ban‐Feng Ruan, Shilu Fan, Huixia Zhu, Wei Tao, Hua Xiao
Abstract
An expedient cyclopropanation of α-methylene-β-lactams with α-ketoesters mediated by P(NMe2)3 has been developed. This reaction enables rapid access to a series of functionalized spirocyclopropyl β-lactams in good yields from bench-stable starting materials under mild conditions. The experimental results indicated that the C3-substituent of the α-methylene-β-lactam not only significantly impacted the reaction efficiency and stereochemistry but also played a pivotal role in determining the chemoselectivity of the reaction.
Topics & Concepts
CyclopropanationLactamMethyleneChemistryStereochemistryMedicinal chemistryOrganic chemistryCatalysisCyclopropane Reaction MechanismsSynthesis of β-Lactam CompoundsAsymmetric Synthesis and Catalysis