Work

Synthesis of chiral sulfilimines by organocatalytic enantioselective sulfur alkylation of sulfenamides

Year: 2024

Type: article

Abstract: Sulfilimines are versatile synthetic intermediates and important moieties in bioactive molecules. However, their applications in drug discovery are underexplored, and efficient asymmetric synthetic methods are highly desirable. Here, we report a transition metal-free pentanidium-catalyzed sulfur alkylation of sulfenamides with exclusive chemoselectivity over nitrogen and high enantioselectivity. The reaction conditions were mild, and a wide range of enantioenriched aryl and alkyl sulfilimines were obtained. The synthetic utility and practicability of this robust protocol were further demonstrated through gram-scale reactions and late-stage functionalization of drugs.

Source: Science Advances

DOI: 10.1126/sciadv.adq2768

Authors: Fucheng Wang, Wanxing Xiang, Yiting Xie, Linge Huai, Luoqiang Zhang, Xin Zhang

Institutions: Sichuan University, State Key Laboratory of Biotherapy

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $4,500

Funder: Fundamental Research Funds for the Central Universities