Amide-Based Morita–Baylis–Hillman Carbonates for Phosphine-Catalyzed Asymmetric (4+2) Annulation
Min Liu , Qihuan Han , Lan Wang , Xi Chen , Xue Zhang , Hongchao Guo
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (24) : 3269 -3277.
Amide-Based Morita–Baylis–Hillman Carbonates for Phosphine-Catalyzed Asymmetric (4+2) Annulation
Comprehensive Summary:Chiral phosphine-catalyzed asymmetric (4+2) annulation of the amide-based Morita–Baylis–Hillman (MBH) carbonates with β, γ-unsaturated butenolides has been developed to give enantiomer-enriched bicyclic δ-lactam γ-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 bicyclic δ-lactam γ-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.
Asymmetric catalysis / Asymmetric synthesis / Phosphine catalysis / Organocatalysis / Cycloaddition / Annulation / Amide / MBH carbonate / Lactam / Piperidinone / Heterocycle
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
/
| 〈 |
|
〉 |
PDF
