Asymmetric Michael addition reaction of 3-substituted-N-Boc oxindoles to activated terminal alkenes catalyzed by a bifunctional tertiary-amine thiourea catalyst

Xin Li; Zhi-Guo Xi; Sanzhong Luo; Jin-Pei Cheng

doi:10.1039/B918644A

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Organic & Biomolecular Chemistry

Issue 1, 2010

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Asymmetric Michael addition reaction of 3-substituted-N-Boc oxindoles to activated terminal alkenes catalyzed by a bifunctional tertiary-amine thiourea catalyst

Xin Li , Zhi-Guo Xi , Sanzhong Luo and Jin-Pei Cheng

Org. Biomol. Chem., 2010, 8, 77-82

DOI: 10.1039/B918644A
Received 09 Sep 2009, Accepted 07 Oct 2009
First published on the web 29 Oct 2009

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The current article reports an organocatalytic strategy for the asymmetric catalysis of chiral oxindoles bearing 3-position all-carbon quaternary stereocenters. Accordingly, highly enantioselective Michael addition reactions of 3-substituted oxindoles to terminal alkenes have been developed by utilizing a bifunctional tertiary-amine thiourea catalyst. The reactions accommodate a number of Michael donor compounds (different substituted 3-aryl or methyl oxindoles), and Michael acceptor compounds (vinyl ketones and vinyl sulfones) to give the desired oxindole products with moderate to excellent yields (up to 99%) and moderate to excellent enantioselectivities (up to 91% ee).

Abstract from Methods in Organic Synthesis 2010

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NMR and HPLC spectra for all the new compounds
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Organic & Biomolecular Chemistry

Asymmetric Michael addition reaction of 3-substituted-N-Boc oxindoles to activated terminal alkenes catalyzed by a bifunctional tertiary-amine thiourea catalyst

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