Organocatalytic Asymmetric Michael Reactions of Cyclic N-Sulfonylimines with Nitroalkenes or 2-Nitroallylic Acetates

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 25, 2025

A highly efficient enantioselective Michael addition of cyclic N-sulfonylimines with nitroalkenes has been developed, utilizing a bifunctional squaramide catalyst. This approach achieves remarkable results, delivering products high yields and outstanding stereoselectivities, reaching up to 97% yield, >20:1 dr, >99% ee. Furthermore, an asymmetric tandem reaction 2-nitroallylic acetates established. innovative methodology involves Michael/intramolecular aza-Michael cascade, leading the formation enantioenriched benzosultam-fused tricyclic compounds excellent stereoselectivities (up dr ee).

Language: Английский

Stereoselective [4+3]-Cycloaddition of 2-Amino-β-nitrostyrenes with Azaoxyallyl Cations to Access Functionalized 1,4-Benzodiazepin-3-ones

Molecules, Journal Year: 2024, Volume and Issue: 29(6), P. 1221 - 1221

Published: March 8, 2024

The 1,4-benzodiazepine structural framework is a fascinating element commonly found in biologically active and pharmaceutically relevant compounds. A highly efficient method for synthesizing 1,4-benzodiazepin-3-ones described, involving [4+3]-cycloaddition reaction between 2-amino-β-nitrostyrenes α-bromohydroxamate, with Cs2CO3 used as base. This process yielded the desired 1,4-benzodiazepines good yields. Furthermore, an organocatalytic asymmetric was successfully accomplished using bifunctional squaramide-based catalyst. approach enabled enantioselective synthesis of chiral commendable yields moderate enantioselectivities, reaching up to 80% yield 72% ee.

Language: Английский

Organocatalytic Enantioselective Synthesis of [5.7]-Fused ε-Sultam N,O-Heterocycles via (3 + 2)-Annulation of Seven-Membered Cyclic N-Sulfonylimines with γ-Hydroxy-α,β-Unsaturated Ketones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(24), P. 18698 - 18706

Published: Dec. 10, 2024

A highly stereoselective protocol for the (3 + 2)-annulation of biphenyl-bridged seven-membered cyclic

Language: Английский