Cascade [1,5]-Hydride Transfer/Cyclization for Synthesis of [3,4]-Fused Oxindoles

Shuai Zhu; Chunqi Chen; Kang Duan; Yun-Ming Sun; Shuai-Shuai Li; Qing Liu; Jian Xiao

doi:10.1021/acs.joc.9b00489

Cascade [1,5]-Hydride Transfer/Cyclization for Synthesis of [3,4]-Fused Oxindoles

J Org Chem. 2019 Jul 5;84(13):8440-8448. doi: 10.1021/acs.joc.9b00489. Epub 2019 Jun 17.

Authors

Shuai Zhu¹, Chunqi Chen¹, Kang Duan¹, Yun-Ming Sun¹, Shuai-Shuai Li¹, Qing Liu², Jian Xiao^{1

3}

Affiliations

¹ Shandong Province Key Laboratory of Applied Mycology, College of Chemistry and Pharmaceutical Sciences , Qingdao Agricultural University , Qingdao 266109 , China.
² College of Chemical and Environmental Engineering , Shandong University of Science and Technology , Qingdao 266590 , China.
³ College of Marine Science and Engineering , Qingdao Agricultural University , Qingdao 266109 , China.

PMID: 31135154
DOI: 10.1021/acs.joc.9b00489

Abstract

The scandium-catalyzed redox-neutral cascade [1,5]-hydride transfer/cyclization between C4-amine-substituted isatins and 1,3-dicarbonyl compounds has been developed. This protocol enabled the synthesis of tricyclic [3,4]-fused oxindoles in good to high yields and excellent diastereoselectivities, featuring high atom- and step economy as well as good functional group tolerance.

Publication types

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