Novel chiral C-1-1 ',2 ',3 ',4 '-tetrahydro-1,1 '-bisisoquinolines: synthesis, resolution, and applications in catalytic enantioselective reactions

作者：Qi Gao; Ji Yao Qiong; Judeh Zaher M A^*

来源：Tetrahedron, 2010, 66(23): 4195-4205.

DOI：10.1016/j.tet.2010.03.106

• Bisisoquinolines
• Bischler-Napieralski reaction
• C-C bond forming reactions
• Henry reaction

A straightforward synthesis of a structurally constrained C-1-1',2',3',4'-tetrahydro-1,1'-bisisoquinoline 1 is described. Resolution of this compound has been achieved successfully. The preparation of chiral N-alkyl, urea, and thiourea derivatives as potential new chiral ligands, based on the parent compound 1, is reported. Chiral compound 1 induced very good selectivity and yield in the addition of either Et2Zn (85% ee, 96% yield) or nitromethane (85% ee, 60% yield) to benzaldehyde.

• 出版日期2010-6-5
• 单位南阳理工学院