C4-Symmetric Inherently Chiral Macrocycles from Organocatalytic Enantioselective Desymmetrization of Resorcin[4]arenes

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-03-28 DOI:10.1021/acscatal.5c00340

Hui Han, Xin-Ge Wang, Shuo Tong, Jieping Zhu, Mei-Xiang Wang

引用次数: 0

Abstract

Reported herein is the synthesis of C₄-symmetric chiral resorcin[4]arene macrocycles by a catalytic enantioselective multicomponent reaction. Using (S)-piperidine-2-carboxamide-derived N,N′-dioxide as a chiral organocatalyst, the desymmetrization of resorcin[4]arenes via a 4-fold Mannich/cyclization reaction produced C₄-symmetric (P_ic)-resorcin[4]arene derivatives in 30%–47% yields with enantiomeric excess (ee) values up to 99%. This one-pot process generated 16 chemical bands in a single operation. The utility of the method was demonstrated by the conversion of the resulting products into functionalized chiral resorcin[4]arenes, which were able to catalyze the asymmetric addition of dialkylzinc to benzaldehydes.

Abstract Image

查看原文本刊更多论文

求助全文

约1分钟内获得全文求助全文

来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.