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Highly enantio- and diastereoselective generation of two quaternary centers in spirocyclopropanation of oxindole derivatives

journal contribution
posted on 08.08.2014 by Artur Noole, Natalia S. Sucman, Mikhail A. Kabeshov, Tonis Kanger, Fliur Z. Macaev, Andrei Malkov
Spirocyclopropanes: only one out of eight possible stereoisomers was obtained in the asymmetric cascade cyclopropanation of alkylidene oxindoles with ethyl 2-chloroacetoacetate. Improved catalyst design ensured that spirocyclopropyl oxindoles featuring two quaternary centers were synthesized in high yield and high enantio-and diastereoselectivity.

Funding

We thank RSC for the International Joint Project grant JP090309 and TUT for travel fellowiship to AN. We acknowledge COST-ORCA action (CM0905) for creating networking and exchange opportunities.

History

School

  • Science

Department

  • Chemistry

Published in

Chemistry - A European Journal

Volume

18

Issue

47

Pages

14929 - 14933

Citation

NOOLE, A. ... et al., 2012. Highly enantio- and diastereoselective generation of two quaternary centers in spirocyclopropanation of oxindole derivatives. Chemistry: a European Journal, 18 (47), pp. 14929-14933.

Publisher

© Wiley-VCH

Version

AM (Accepted Manuscript)

Publication date

2012

Notes

This is the peer reviewed version of the following article: NOOLE, A. ... et al., 2012. Highly enantio- and diastereoselective generation of two quaternary centers in spirocyclopropanation of oxindole derivatives. Chemistry: a European Journal, 18 (47), pp. 14929-14933, which has been published in final form at: http://dx.doi.org/10.1002/chem.201203099.

ISSN

0947-6539

eISSN

1521-3765

Language

en

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