期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 7, 期 -, 页码 410-420出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.7.53
关键词
allenamides; 2-amido-dienes; 3-amido-trienes; electrocyclic ring-closure; 1,3-hydrogen shift; isomerization
资金
- NIH [GM066055]
Preparations of de novo acyclic 2-amido-dienes and 3-amido-trienes through 1,3-hydrogen shifts from allenamides are described. These 1,3-hydrogen shifts could be achieved thermally or they could be promoted by the use of Bronsted acids. Under either condition, these processes are highly regioselective in favour of the a-position, and highly stereoselective in favour of the E-configuration. In addition, 6 pi-electron electrocyclic ring-closure could be carried out with 3-amido-trienes to afford cyclic 2-amido-dienes, and such electrocyclic ring-closure could be rendered in tandem with the 1,3-hydrogen shift.
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