期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 15, 页码 5622-5625出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo900764s
关键词
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资金
- National Natural Sciences Foundation of China [20602006]
- Department of Science and Technology of JLSDG [20080548, 20082212]
- Training Fund of NENUS Scientific Innovation Project [NENU-STC07017, NENU-STB07007]
A simple and highly efficient three-component reaction of the readily available alpha-cinnamoyl ketene-S,S-acetals 1 with oxalyl chloride has been developed and the corresponding gamma-alkylidenebutenolides 2 were obtained stereospecifically in excellent yields under very mild conditions. On the basis of this reaction, a series of highly functionalized bicyclo[3.3.1]nonanes 3 were constructed in good to high yields in an atom-economic manner with good diastereoselectivity via a BF(3)center dot OEt(2)-mediated novel tandem double cyclization of gamma-alkylidenebutenolides 2 under very mild conditions.
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