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Catalytic Asymmetric Synthesis of Morpholines. Using Mechanistic Insights To Realize the Enantioselective Synthesis of Piperazines

Ying Yin Lau, Huimin Zhai and Laurel L. Schafer*

*Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia V6T 1Z1, Canada, Email: schaferchem.ubc.ca

Y. Y. Lau, H. Zhai, L. L. Schafer, J. Org. Chem., 2016, 81, 8696-8709.

DOI: 10.1021/acs.joc.6b01884 (free Supporting Information)


Abstract

A tandem sequential one-pot reaction employing both hydroamination and asymmetric transfer hydrogenation reactions enables an efficient and practical enantioselective synthesis of 3-substituted morpholines from aminoalkyne substrates. A wide range of functional groups is tolerated. Hydrogen-bonding interactions between the oxygen and the [(S,S)-Ts-DPEN] ligand of the Ru catalyst are crucial for obtaining high ee's.

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Key Words

morpholines, formic acid


ID: J42-Y2016