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Wang Y, Wang Q, Zhu J. Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates. Chemistry. 2016;22(24):8084-8doi: 10.1002/chem.201601548.
Wang, Y., Wang, Q., & Zhu, J. (2016). Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates. Chemistry (Weinheim an der Bergstrasse, Germany), 22(24), 8084-8. https://doi.org/10.1002/chem.201601548
Wang, Yang, et al. "Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,24 (2016): 8084-8. doi: https://doi.org/10.1002/chem.201601548
Wang Y, Wang Q, Zhu J. Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates. Chemistry. 2016 Jun 06;22(24):8084-8. doi: 10.1002/chem.201601548. Epub 2016 May 02. PMID: 27135440.
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Chemistry. 2016 Jun 06;22(24):8084-8. doi: 10.1002/chem.201601548. Epub 2016 May 02.

Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates.

Chemistry (Weinheim an der Bergstrasse, Germany)

Yang Wang, Qian Wang, Jieping Zhu

Affiliations

  1. Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
  2. Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland. [email protected].

PMID: 27135440 DOI: 10.1002/chem.201601548

Abstract

The first catalytic asymmetric inverse electron demand 1,3-dipolar cycloaddition of azomethine imines with enecarbamates has been developed. Isoquinoline-fused pyrazolidines containing two or three contiguous stereogenic centers were obtained in high yields with excellent regio-, diastereo-, and enantioselectivities. The pyrazolidine ring can be opened to install an aminal, α-amino nitrile, or homoallylamine function with an excellent control of the newly generated stereogenic center. Access to aminobenzo[a]quinolizidine is also documented.

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

Keywords: azomethines; carbamates; cycloaddition; organocatalysis; tetrahydroisoquinolines

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