Issue 87, 2016, Issue in Progress

Organocatalytic tandem enantioselective Michael-cyclization of isatin-derived β,γ-unsaturated α-ketoesters with 3-hydroxy-4H-chromen-4-one or 2-hydroxy-1,4-naphthoquinone derivatives

Abstract

The enantioselective formal [3 + 3] annulation reaction of isatin-derived β,γ-unsaturated α-ketoesters with 3-hydroxy-4H-chromen-4-ones or 2-hydroxy-1,4-naphthoquinone was successfully implemented under catalysis of quinine-derived bifunctional tertiary amine-thiourea catalysts. The efficient tandem Michael-cyclization has provided facile access to optically active spiro[oxindole-pyrano[3,2-b]chromenone] and spiro[oxindole-benzo[g]chromene-dione] derivatives in high yields with excellent diastereo- and enantioselectivities.

Graphical abstract: Organocatalytic tandem enantioselective Michael-cyclization of isatin-derived β,γ-unsaturated α-ketoesters with 3-hydroxy-4H-chromen-4-one or 2-hydroxy-1,4-naphthoquinone derivatives

Supplementary files

Article information

Article type
Paper
Submitted
07 Jul 2016
Accepted
19 Aug 2016
First published
19 Aug 2016

RSC Adv., 2016,6, 84248-84254

Organocatalytic tandem enantioselective Michael-cyclization of isatin-derived β,γ-unsaturated α-ketoesters with 3-hydroxy-4H-chromen-4-one or 2-hydroxy-1,4-naphthoquinone derivatives

S. Yin, S. Zhang, J. Zhang, B. Sun, W. Fan, B. Wu and X. Wang, RSC Adv., 2016, 6, 84248 DOI: 10.1039/C6RA17400K

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