4.7 Article

Ruthenium-Catalyzed Chemo- and Enantioselective Hydrogenation of Isoquinoline Carbocycles

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 7, Pages 3829-3839

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00190

Keywords

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Funding

  1. JSPS [JP16H04149, JP15KT0066]
  2. advanced Graduate Program on Molecular Systems for Devices, Program for Leading Graduate Schools
  3. Grants-in-Aid for Scientific Research [15KT0066] Funding Source: KAKEN

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A chemoselective hydrogenation of isoquinoline carbocydes was achieved by using the catalyst prepared from Ru(methallyl)(2)(cod) and trans-chelate chiral ligand PhTRAP. The unique chemoselectivity achieved in this hydrogenation could be ascribed to the trans-chelation of the chiral ligand. The procedure for preparing the catalyst strongly affects the reproducibility of the carbocyde hydrogenation. Various 5-, 6-, 7-, and 8-substituted isoquinolines were selectively hydrogenated at their carbocycles to afford 5,6,7,8-tetrahydroisoquinolines as major products in high yields with moderate or good enantioselectivities. Some mechanistic studies suggested that the stereogenic center was created during the initial addition of H-2 to the aromatic ring in the hydrogenation of 5-substituted isoquinolines. In other words, the stereochemical control was accompanied by the dearomatization.

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