Inherently Chiral Seven- and Eight-Membered Rings: Enantioselective Synthesis and Applications

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 17, 2025

Compared to smaller or larger rings, seven- and eight-membered carbo- heterocycles are typically nonplanar exhibit greater conformational rigidity. This property alone can impart chirality certain 7- 8-membered ring systems. Herein, we summarize recent achievements in the enantioselective synthesis of this class inherently chiral medium including both construction modification, as well applications ligands catalysts derived from these rigid cyclic scaffolds asymmetric catalysis.

Language: Английский

Catalytic Enantioselective Chlorofunctionalizations of N-Substituted Amides Using In Situ Generated HOCl as Hydrogen Bond Source

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 29, 2025

Asymmetric organocatalytic halocyclization represents a powerful method for the synthesis of valuable chiral haloheterocycles. However, its heavy dependence on substrates that contain hydrogen bond donors enantiocontrol limits broader application. Here we report catalytic asymmetric chlorofunctionalization olefinic amides do not bear donors, allowing efficient production chlorooxazolidin-2-ones and chloroamino esters featuring quaternary stereocenters, achieved with high yields excellent enantioselectivity. This protocol facilitates N-aryloxazolidin-2-ones establishes useful framework synthesizing antibiotic analogues. Mechanistic studies indicate trace amounts water interact chlorinating agent to produce HOCl in situ, which acts as both proton donor hypochlorite source, thereby promoting cyclization process. strategy significantly broadens potential development diverse array functional molecules.

Language: Английский