期刊
ORGANIC LETTERS
卷 12, 期 24, 页码 5620-5623出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol102283c
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资金
- MICINN of Spain [CTQ2008-00763/BQU, CTQ2010-19774-0O2-01]
- Generalitat de Catalunya [2009SGR 00901]
- IRB Barcelona
Stoichiometric and catalytic intermolecular Pauson Khand reactions (PKRs) of dissymmetric fluorinated alkynes were performed, affording regioselectively a-fluorinated cyclopentenones. Ethyl 4,4,4-trifluorobutynoate was an excellent substrate; Its reaction with norbornadiene gave the corresponding PKR adduct in good yield and complete regioselectivity. Conjugate addition of nitroalkanes or cyanide to this adduct is stereospecific and entails concomitant loss of a trifluoromethyl group. This reaction can be exploited to prepare cyclopentenones featuring quaternary centers.
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