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Engl OD, Fritz SP, Wennemers H. Stereoselective Organocatalytic Synthesis of Oxindoles with Adjacent Tetrasubstituted Stereocenters. Angew Chem Int Ed Engl. 2015;54(28):8193-7doi: 10.1002/anie.201502976.
Engl, O. D., Fritz, S. P., & Wennemers, H. (2015). Stereoselective Organocatalytic Synthesis of Oxindoles with Adjacent Tetrasubstituted Stereocenters. Angewandte Chemie (International ed. in English), 54(28), 8193-7. https://doi.org/10.1002/anie.201502976
Engl, Oliver D, et al. "Stereoselective Organocatalytic Synthesis of Oxindoles with Adjacent Tetrasubstituted Stereocenters." Angewandte Chemie (International ed. in English) vol. 54,28 (2015): 8193-7. doi: https://doi.org/10.1002/anie.201502976
Engl OD, Fritz SP, Wennemers H. Stereoselective Organocatalytic Synthesis of Oxindoles with Adjacent Tetrasubstituted Stereocenters. Angew Chem Int Ed Engl. 2015 Jul 06;54(28):8193-7. doi: 10.1002/anie.201502976. Epub 2015 Jun 01. PMID: 26033441.
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Angew Chem Int Ed Engl. 2015 Jul 06;54(28):8193-7. doi: 10.1002/anie.201502976. Epub 2015 Jun 01.

Stereoselective Organocatalytic Synthesis of Oxindoles with Adjacent Tetrasubstituted Stereocenters.

Angewandte Chemie (International ed. in English)

Oliver D Engl, Sven P Fritz, Helma Wennemers

Affiliations

  1. ETH Zurich, Laboratory for Organic Chemistry, D-CHAB, Vladimir-Prelog-Weg 3, 8093 Zurich (Switzerland) http://www.wennemers.ethz.ch.
  2. ETH Zurich, Laboratory for Organic Chemistry, D-CHAB, Vladimir-Prelog-Weg 3, 8093 Zurich (Switzerland) http://www.wennemers.ethz.ch. [email protected].

PMID: 26033441 DOI: 10.1002/anie.201502976

Abstract

Oxindoles with adjacent tetrasubstituted stereocenters were obtained in high yields and stereoselectivities by organocatalyzed conjugate addition reactions of monothiomalonates (MTMs) to isatin-derived N-Cbz ketimines. The method requires only a low catalyst loading (2 mol %) and proceeds under mild reaction conditions. Both enantiomers are accessible in good yields and excellent stereoselectivities by using either Takemoto's catalyst or a cinchona alkaloid derivative. The synthetic methodology allowed establishment of a straightforward route to derivatives of the gastrin/cholecystokinin-B receptor antagonist AG-041R.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: asymmetric synthesis; enantioselectivity; heterocycles; organocatalysis; synthetic methods

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