Issue 70, 2018

Highly stereoselective spirocyclopropanation of various diazooxindoles with olefins catalyzed using Ru(ii)-complex

Abstract

Optically active spirocyclopropyloxindole derivatives were efficiently synthesized from diazooxindoles and olefins in the presence of a Ru(II)-Pheox catalyst. Among a series of Ru(II)-Pheox catalysts, Ru(II)-Pheox 6e was determined to be the best catalyst for spirocyclopropanation reactions of diazooxindoles with various olefins in high yields (up to 98%) with high diastereoselectivities (up to trans:cis = >99:1<) and enantioselectivities (up to 99% ee). Furthermore, as the first catalytic asymmetric synthesis, anti-HIV active candidate 4a and a bioactive compound of AMPK modulator 4c were easily synthesized from the corresponding diazooxindoles 1i and 1b, respectively, in high yields with high enantioselectivities (4a: 82% yield, 95% ee, 4b: 99% yield, 93% ee).

Graphical abstract: Highly stereoselective spirocyclopropanation of various diazooxindoles with olefins catalyzed using Ru(ii)-complex

Supplementary files

Article information

Article type
Paper
Submitted
07 noy 2018
Accepted
20 noy 2018
First published
28 noy 2018
This article is Open Access
Creative Commons BY license

RSC Adv., 2018,8, 39865-39869

Highly stereoselective spirocyclopropanation of various diazooxindoles with olefins catalyzed using Ru(II)-complex

M. Tone, Y. Nakagawa, S. Chanthamath, I. Fujisawa, N. Nakayama, H. Goto, K. Shibatomi and S. Iwasa, RSC Adv., 2018, 8, 39865 DOI: 10.1039/C8RA09212E

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