Deoxygenative Cyclopropanation of Aldehydes with Acyl‐Stabilized Sulfur Ylides

Chemistry - A European Journal, Journal Year: 2025, Volume and Issue: unknown

Published: March 5, 2025

Herein, we described a novel [1+1+1] deoxygenative cyclopropanation between sulfur ylides and aldehydes, which is distinctive from traditional epoxidation reactions. The method offers straightforward approach for the synthesis of highly stereoselective, functionalized, structurally diverse tertiary cyclopropyl thioethers. reaction demonstrates broad substrate scope excellent compatibility with various functional groups, rendering it particularly suitable late-stage modifications pharmaceuticals natural products, as well compounds. Additionally, β,β-disubstituted enals can also engage in reaction, instead undergoing classic through Michael addition reaction-induced cyclization ylides, thus yielding synthetically important vinylcyclopropanes chemoselectivity diastereoselectivity.

Language: Английский

The Synthesis of Benzazepines via Sequential [3 + 2]-Annulation and [3,3]-Sigmatropic Rearrangement

Organic Letters, Journal Year: 2024, Volume and Issue: 26(48), P. 10224 - 10228

Published: Nov. 22, 2024

A novel annulation reaction of prop-2-ynylsulfonium salts with sulfur ylides and nitrosobenzenes has been developed, affording various benzazepines in moderate to good yields. Prop-2-ynylsulfonium act as C

Language: Английский

Synthesis of 4-Hydroxy-5-phenylaminoimidazoles through a Three-Component Reaction of Sulfur Ylides, Nitrosobenzenes, and Amidines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(24), P. 18227 - 18234

Published: Nov. 27, 2024

A novel annulation reaction of amidines with sulfur ylides and nitrobenzenes has been developed, affording various 4-hydroxy-5-phenylaminoimidazoles in moderate to excellent yields. The have further converted into α-ketoamide imidazol-4-imine derivatives. Moreover, a plausible mechanism for this multicomponent is proposed.

Language: Английский