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Tahara YK, Matsubara R, Mitake A, et al. Catalytic and Enantioselective Synthesis of Chiral Multisubstituted Tribenzothiepins by Intermolecular Cycloadditions. Angew Chem Int Ed Engl. 2016;55(14):4552-6doi: 10.1002/anie.201511876.
Tahara, Y. K., Matsubara, R., Mitake, A., Sato, T., Kanyiva, K. S., & Shibata, T. (2016). Catalytic and Enantioselective Synthesis of Chiral Multisubstituted Tribenzothiepins by Intermolecular Cycloadditions. Angewandte Chemie (International ed. in English), 55(14), 4552-6. https://doi.org/10.1002/anie.201511876
Tahara, Yu-Ki, et al. "Catalytic and Enantioselective Synthesis of Chiral Multisubstituted Tribenzothiepins by Intermolecular Cycloadditions." Angewandte Chemie (International ed. in English) vol. 55,14 (2016): 4552-6. doi: https://doi.org/10.1002/anie.201511876
Tahara YK, Matsubara R, Mitake A, Sato T, Kanyiva KS, Shibata T. Catalytic and Enantioselective Synthesis of Chiral Multisubstituted Tribenzothiepins by Intermolecular Cycloadditions. Angew Chem Int Ed Engl. 2016 Mar 24;55(14):4552-6. doi: 10.1002/anie.201511876. Epub 2016 Mar 02. PMID: 26933763.
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Angew Chem Int Ed Engl. 2016 Mar 24;55(14):4552-6. doi: 10.1002/anie.201511876. Epub 2016 Mar 02.

Catalytic and Enantioselective Synthesis of Chiral Multisubstituted Tribenzothiepins by Intermolecular Cycloadditions.

Angewandte Chemie (International ed. in English)

Yu-Ki Tahara, Riku Matsubara, Akihito Mitake, Tatsuki Sato, Kyalo Stephen Kanyiva, Takanori Shibata

Affiliations

  1. Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo, 169-8555, Japan.
  2. International Center for Science and Engineering Programs (ICSEP), Waseda University, Shinjuku, Tokyo, 169-8555, Japan.
  3. Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo, 169-8555, Japan. [email protected].
  4. JST, ACT-C, Kawaguchi, Saitama, 332-0012, Japan. [email protected].

PMID: 26933763 DOI: 10.1002/anie.201511876

Abstract

The first catalytic and highly enantioselective synthesis of tribenzothiepin derivatives was achieved. Two types of intermolecular cycloadditions using either diphenyl-sulfide-tethered diynes or 2-phenyl sulfanylbenzene-tethered diynes with a monoalkyne successfully gave chiral multisubstituted tribenzothiepins in good to excellent ee values under mild conditions. The inversion energy of this saddle-shaped molecule was calculated by measurement of the racemization rate of chiral tribenzothiepins using the Eyring kinetic equation under heating conditions. The present protocol could also be used to prepare a chiral tribenzoselenepin.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: chirality; cycloaddition; enantioselectivity; rhodium; synthetic methods

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