Work

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

Year: 2025

Type: article

Abstract: Reported herein is the synthesis of C 4 -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 C 4 -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.

Source: ACS Catalysis

DOI: 10.1021/acscatal.5c00340

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

Institutions: Tsinghua University, École Polytechnique Fédérale de Lausanne

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Natural Science Foundation of China, Tsinghua University

Awards: G1698011894, G2376201943, G2705051328, G8209979106, G8783813858