期刊
TETRAHEDRON
卷 66, 期 11, 页码 1990-1993出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.01.058
关键词
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资金
- National Science Foundation of China [20725206, 20732004]
- Specialized Research Fund for the Doctoral Program of Higher Education in China
- US National Science Foundation [CHE-0717995]
- American Chemical Society
A novel C-1 symmetric BINOL-terpyridine ligand (R)-5 is synthesized. This ligand in combination with ZnEt2 and Ti((OPr)-Pr-1)(4) is found to catalyze the highly enantioselective reaction (up to 98% ee) of methyl propiolate with a variety of aromatic aldehydes at 0 degrees C to give the synthetically useful gamma-hydroxy-alpha,beta-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. (C) 2010 Elsevier Ltd. All rights reserved.
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