Cinchona Alkaloid Derived Iodide Catalyzed Enantioselective Oxidative α-Amination of Carbonyl Compounds toward the Construction of Spiroindolyloxindole

Dangui Wang; Wentao Zhang; Xunbo Lu; Hongwei Zhou; Fangrui Zhong

doi:10.1021/acs.orglett.1c04118

Cinchona Alkaloid Derived Iodide Catalyzed Enantioselective Oxidative α-Amination of Carbonyl Compounds toward the Construction of Spiroindolyloxindole

Org Lett. 2022 Jan 28;24(3):842-847. doi: 10.1021/acs.orglett.1c04118. Epub 2022 Jan 13.

Authors

Dangui Wang^{1

2}, Wentao Zhang², Xunbo Lu², Hongwei Zhou³, Fangrui Zhong²

Affiliations

¹ School of Pharmacy, Weifang Medical University, Weifang 261053, People's Republic of China.
² Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Engineering Research Center for Biomaterials and Medical Protective Materials, Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology (HUST), 1037 Luoyu Road, Wuhan 430074, People's Republic of China.
³ College of Biological, Chemical Science and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, People's Republic of China.

PMID: 35025513
DOI: 10.1021/acs.orglett.1c04118

Abstract

Novel cinchona alkaloid derived iodide catalysts were developed for the enantioselective oxidative α-amination of 2-oxindoles, providing various functionalized spiropyrrolidine oxindoles in high yields and with good enantioselectivities. This iodide/ROOH catalytic system features a one-step synthesis of a catalyst with multiple functionalities, ease of operation, and good scalability, thereby enriching the repertoire of iodide catalysis for enantioselective oxidative coupling reactions.

Publication types

Research Support, Non-U.S. Gov't