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

Yang Wang; Qian Wang; Jieping Zhu

doi:10.1002/chem.201601548

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

Chemistry. 2016 Jun 6;22(24):8084-8. doi: 10.1002/chem.201601548. Epub 2016 May 2.

Authors

Yang Wang¹, Qian Wang¹, Jieping Zhu²

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. jieping.zhu@epfl.ch.

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.

Keywords: azomethines; carbamates; cycloaddition; organocatalysis; tetrahydroisoquinolines.

Publication types

Research Support, Non-U.S. Gov't