Work

Enantioselective synthesis of C–C and C–N axially chiral pyrazole-based heterobiaryls

Year: 2025

Type: article

Abstract: Axially chiral five-membered heteroaryls are prevalent in bioactive molecules. Their catalytic asymmetric synthesis remains challenging due to their relatively low rotational energy barriers. We developed a chiral nickel(ii) complex-catalyzed asymmetric cycloaddition/oxidation sequential reaction of hydrazonoyl chlorides with α,β-unsaturated enones, which involves asymmetric [3 + 2] 1,3-dipolar cycloaddition of hydrazonoyl chlorides with α,β-unsaturated enones followed by oxidation to realize central-to-axial chirality transfer. A class of pyrazole-based heterobiaryls were prepared efficiently with high yields and good enantioselectivities. Based on the mechanistic study and control experiments, a possible mechanism was proposed to elucidate the reaction process and enantioinduction.

Source: Chemical Science

DOI: 10.1039/d5sc06841j

Authors: Jun He, Zun Yang, Lili Lin, Xiaoming Feng

Institution: Sichuan University

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Natural Science Foundation of China, Sichuan University, National Key Research and Development Program of China

Awards: G7280560933, G7583187518