Amide-Based Morita–Baylis–Hillman Carbonates for Phosphine-Catalyzed Asymmetric(4+2)Annulation  

作　　者：Min Liu Qihuan Han Lan Wang Xi Chen Xue Zhang Hongchao Guo 

机构地区：[1]Department of Chemistry,China Agricultural University,Beijing 100193,China [2]State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China

出　　处：《Chinese Journal of Chemistry》2024年第24期3269-3277,共9页中国化学(英文版)

基　　金：supported by the National Natural Science Foundation of China(Nos.21871293,22071264).

摘　　要：Chiral phosphine-catalyzed asymmetric(4+2)annulation of the amide-based Morita–Baylis–Hillman(MBH)carbonates withβ,γ-unsaturated butenolides has been developed to give enantiomer-enriched bicyclicδ-lactamγ-butyrolactone compounds.The amide-based MBH carbonates were first used as acceptor and aza-C4 synthon in phosphine catalysis.Under mild reaction conditions,a variety of amide-based MBH carbonates and unsaturated butenolides were well tolerated to provide chiral bicyclicδ-lactamγ-butyrolactone derivatives in high yields with excellent enantioselectivities as well as diastereoselectivities.A plausible reaction mechanism was also proposed based on control experiments and DFT calculations.

关 键 词：Asymmetric catalysis Asymmetric synthesis Phosphine catalysis Organocatalysis Cycloaddition ANNULATION AMIDE MBH carbonate LACTAM Piperidinone Heterocycle 

分 类 号：O62[理学—有机化学]