期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 351, 期 7-8, 页码 1014-1018出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900054
关键词
allylic substitution; C-C bond formation; copper; organozinc reagents; phosphane ligands
资金
- Ministry of Education, Culture, Sports, Science and Technology of Japan [18105004, 19750026]
- Global COE Program for Chemistry Innovation
- Grants-in-Aid for Scientific Research [19750026] Funding Source: KAKEN
A proline-derived aminohydroxyphosphine ligand induced excellent regio- and enantioselectivities (S(N)2':S(N)2>94:6, 94-97% ee) in the copper-catalyzed substitution reaction of cinnamyl phosphates with Et2Zn. A computational modelling, study of the reaction pathway suggests that the displacement of the leaving group takes place In an ordered, anti-fashion through simultaneous copper-olefin and zinc-oxygen interactions, which is critical for the enantioselection.
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