期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 7, 期 -, 页码 1249-1254出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.7.145
关键词
benzylic metalation; LiNK chemistry; [2.2]metacyclophane; oxidative coupling; planar chirality
资金
- Science Foundation Ireland
- Irish Research Council for Science, Engineering and Technology
- ERA-Chemistry
A new two-step general approach to [2.2]metacyclophane synthesis from substituted m-xylenes is described. The strategy employs a selective benzylic metalation and oxidative C-C bond formation for both synthetic operations. Regioselective benzylic metalation is achieved using the BuLi, KOt-Bu, TMP(H) (2,2,6,6-tetramethylpiperidine) combination (LiNK metalation conditions) and oxidative coupling with 1,2-dibromoethane. The synthetic ease of this approach compares favourably with previously reported methods and allows for ready access to potentially useful planar chiral derivatives.
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