Enantioselective synthesis of tetrahydrocyclopenta[b]indole bearing a chiral quaternary carbon center via Pd(II)–SPRIX-catalyzed C–H activation

Mohamed Ahmed Abozeid; Shiho Sairenji; Shinobu Takizawa; Makoto Fujita; Hiroaki Sasai

doi:10.1039/C7CC03199H

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Enantioselective synthesis of tetrahydrocyclopenta[b]indole bearing a chiral quaternary carbon center via Pd(ii)–SPRIX-catalyzed C–H activation†

Mohamed Ahmed Abozeid,

^ab Shiho Sairenji,

^c Shinobu Takizawa,

*^a Makoto Fujita^c and Hiroaki Sasai*^a

Author affiliations

* Corresponding authors

^a The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan
E-mail: taki@sanken.osaka-u.ac.jp, sasai@sanken.osaka-u.ac.jp

^b Department of Chemistry, Faculty of Science, Mansoura University, El-Gomhoria Street, Mansoura, Egypt

^c Department of Applied Chemistry, Graduate School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, Japan

Abstract

The highly enantioselective cyclization of 3-alkenylindole via C–H activation has been established using Pd(OCOCF₃)₂ in conjunction with the chiral spiro bis(isoxazoline) ligand (SPRIX). The presence of an N-allyl substituent on the substrate has a strong impact on both reactivity and selectivity, leading to tricyclic indole products (up to 96% ee) with a chiral quaternary carbon center.

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C7CC03199H
Article type: Communication
Submitted: 25 Apr 2017
Accepted: 06 Jun 2017
First published: 06 Jun 2017

Download Citation

Chem. Commun., 2017,53, 6887-6890

Permissions

Request permissions

Enantioselective synthesis of tetrahydrocyclopenta[b]indole bearing a chiral quaternary carbon center via Pd(II)–SPRIX-catalyzed C–H activation

M. A. Abozeid, S. Sairenji, S. Takizawa, M. Fujita and H. Sasai, Chem. Commun., 2017, 53, 6887 DOI: 10.1039/C7CC03199H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Chemical Communications

Enantioselective synthesis of tetrahydrocyclopenta[b]indole bearing a chiral quaternary carbon center via Pd(ii)–SPRIX-catalyzed C–H activation†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Enantioselective synthesis of tetrahydrocyclopenta[b]indole bearing a chiral quaternary carbon center via Pd(II)–SPRIX-catalyzed C–H activation

Social activity

Search articles by author

Spotlight

Advertisements