期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 14, 期 -, 页码 576-582出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.14.44
关键词
asymmetric methylation; chiral phosphine ligand; copper catalyst; dimethylzinc; trifluoropyruvate
资金
- JST (ACT-C: Advanced Catalytic Transformation program for Carbon utilization)
- JSPS KAKENHI [25410036]
- Noguchi Institute
- Grants-in-Aid for Scientific Research [25410036, 16K05686] Funding Source: KAKEN
The catalytic asymmetric methylation of fluoroalkylated pyruvates is shown with dimethylzinc as a methylating reagent in the presence of a copper catalyst bearing a chiral phosphine ligand. This is the first catalytic asymmetric methylation to synthesize various alpha-fluoroalkylated tertiary alcohols with CF3, CF2H, CF2Br, and n-CnF2n+1 (n = 2, 3, 8) groups in good-to-high yields and enantioselectivities. Axial backbones and substituents on phosphorus atoms of chiral phosphine ligands critically influence the enantioselectivity. Moreover, the methylation of simple perfluoroalkylated ketones is found to be facilitated by only chiral phosphines with-out copper.
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