Enantioselective Synthesis of Spiroindolines via Cascade Isomerization/Spirocyclization/Dearomatization Reaction
By: Pan, Zhiqiang; Liu, Yuchang; Hu, Fengchi; Liu, Qinglong; Shang, Wenbin; Ji, Xu; Xia, Chengfeng
Organic letters
Volume:22 Issue:4 Pages:1589-1593
DOI:10.1021/acs.orglett.0c00181
Published: 2020-Feb-21 (Epub 2020 Jan 28)
Document Type:Journal Article
Abstract
The spiroindoline skeleton featured with 2,7-diazaspiro[4.4]nonane exists in various structurally intricate and biologically active monoterpene indole alkaloids. A catalytic asymmetric cascade enamine isomerization/spirocyclization/dearomatization succession to construct the spiroindoline was developed, which employed the indolyl dihydropyridine as a substrate under catalysis of the chiral phosphoric acid. This cascade reaction provided various spiroindolines in both diastereoselective and enantionselective fashions.
Author Information
Addresses:Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education and Yunnan Province), School of Chemical Science and Technology , Yunnan University , Kunming 650091 , China.
https://pubs.acs.org/doi/10.1021/acs.orglett.0c00181
