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Issue 57, 2018
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Cu(II)–tBu–PHOX catalyzed enantioselective malonate addition onto 3-hydroxy 2-oxindoles: application in the synthesis of dimeric pyrroloindoline alkaloids

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Abstract

An efficient Cu(II)–PHOX-catalyzed malonate addition onto 3-hydroxy 3-indolyl-2-oxindoles is envisioned to afford excellent enantioselectivities (up to >99% ee) in high chemical yields. Detailed characterization techniques including X-ray, NMR, CV and EPR experiments suggest that a Cu(II)-complex is involved as an active species in this process. Applying this strategy, an advanced intermediate of cyclotryptamine alkaloids has been synthesized in few steps for a general approach to bis-cyclotryptamine alkaloids.

Graphical abstract: Cu(ii)–tBu–PHOX catalyzed enantioselective malonate addition onto 3-hydroxy 2-oxindoles: application in the synthesis of dimeric pyrroloindoline alkaloids

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Publication details

The article was received on 31 May 2018, accepted on 12 Jun 2018 and first published on 18 Jun 2018


Article type: Communication
DOI: 10.1039/C8CC04338H
Citation: Chem. Commun., 2018,54, 7963-7966
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    Cu(II)–tBu–PHOX catalyzed enantioselective malonate addition onto 3-hydroxy 2-oxindoles: application in the synthesis of dimeric pyrroloindoline alkaloids

    K. N. Babu, L. K. Kinthada, P. Pratim Das and A. Bisai, Chem. Commun., 2018, 54, 7963
    DOI: 10.1039/C8CC04338H

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