Issue 8, 2015

Catalytic enantioselective synthesis of quaternary 3,3′-indolyloxindoles by combination of Rh(ii) complexes and chiral phosphines

Abstract

Rh(II)/chiral phosphine combined catalysis has been developed for a highly efficient sequential C–H functionalization/asymmetric allylation or Michael addition reaction of indoles and 3-diazooxindoles with allenoates or vinyl ketones to afford a diverse range of quaternary 3,3′-indolyloxindole derivatives. Moreover, a significantly positive effect of LiCl in the sequential C–H functionalization/allylation reaction was observed, which led to an unusual ternary activation mechanism in the allylation step.

Graphical abstract: Catalytic enantioselective synthesis of quaternary 3,3′-indolyloxindoles by combination of Rh(ii) complexes and chiral phosphines

Supplementary files

Article information

Article type
Research Article
Submitted
07 Cam 2015
Accepted
02 Wax 2015
First published
03 Wax 2015

Org. Chem. Front., 2015,2, 956-960

Author version available

Catalytic enantioselective synthesis of quaternary 3,3′-indolyloxindoles by combination of Rh(II) complexes and chiral phosphines

D. Chen, C. Zhang, Y. Hu, Z. Han and L. Gong, Org. Chem. Front., 2015, 2, 956 DOI: 10.1039/C5QO00151J

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