期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 20, 页码 7684-7689出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo901340v
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资金
- Natural Sciences Foundation of China [20821002, 20672131]
- Major State Basic Research Development Program [2009CB825300]
- Chinese Academy of Sciences
- Science and Technology Commission of Shanghai Municipality
Cu(SbF6)(2)-catalyzed reaction of 2-substituted cyclopropane-1,1-dicarboxylates 1 with enol silyl ethers 2 call be readily controlled: the reaction undergoes a cycloaddition to provide substituted cyclopentane derivatives 3 in excellent yields with high diastereoselectivities in the presence of complex 8/Cu(II); however, the same substrates afford acyclic 1,6-dicarbonyl products 4 via a cycloaddition-ring-opening reaction in tip to 92% yield in the absence of ligand 8. The mechanism for the ligand-switchable reactions was investigated by both control experiments and H-1 NMR studies. The substrate scope and limitation of the tunable transformation were also examined.
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