Synthesis of a C1 symmetric BINOL-terpyridine ligand and highly enantioselective methyl propiolate addition to aromatic aldehydes |
| |
| Authors: | Xi Chen Li Wang De-Shun Huang |
| |
| Institution: | a Department of Chemistry, Key Laboratory of Green Chemistry and Technology (Ministry of Education), Sichuan University, Chengdu 610064, China
b Department of Chemistry, University of Virginia, McCormick Road, Charlottesville, VA 22904-4319, USA |
| |
| Abstract: | A novel C1 symmetric BINOL-terpyridine ligand (R)-5 is synthesized. This ligand in combination with ZnEt2 and Ti(OiPr)4 is found to catalyze the highly enantioselective reaction (up to 98% ee) of methyl propiolate with a variety of aromatic aldehydes at 0 °C to give the synthetically useful γ-hydroxy-α,β-acetylenic esters. In comparison with the previously reported BINOL system, the use of (R)-5 requires a reduced amount of the chiral ligand without the addition of a Lewis base. It shows higher enantioselectivity for a number of substrates. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
