FULL PAPERS
method. In addition, the scale-up reaction for preparing 2a
on a 10 mmol scale is also similar to this procedure except
for changing the corresponding amounts of reagents and pu-
rification using silica column chromatography.
Center of HUST. The Chutian Scholar Program of the Hubei
Provincial Government and the Cooperative Innovation
Center of Hubei Province are also acknowledged. This work
is also supported by the Fundamental Research Funds for the
Central Universities of China (2014ZZGH019).
Typical Procedure for the Synthesis of 5a–5l
In a typical reaction, 2-diazo-5,5-dimethylcyclohexane-1,3-
dione (0.166 g, 1.0 mmol), 1-(vinyloxy)butane (0.50 g,
5.0 mmol), and HCP–PPh3–Ru II (40 mg, 0.006 mmol) were
added to toluene (2 mL). The mixture was stirred for 10 h at
1008C. After reaction completion, the mixture was cooled
to room temperature and then centrifuged. The supernatant
organic phase was isolated, and the bottom solid was
washed with ethyl acetate (2.0 mL ꢂ 3). All organic phases
were combined, dried over anhydrous Na2SO4, and then
concentrated under reduced pressure. Afterwards, the de-
sired product 5a was obtained by isolation using preparative
TLC [eluting solvent: ethyl acetate/petroleum ether=1/5 (v/
v)]; yield: 0.20 g (85%). The procedures for synthesizing 5b–
5l are similar to this method. In addition, the scale-up reac-
tion for preparing 5a on a 10 mmol scale is also similar to
this procedure except changing the corresponding amounts
of reagents and purification using silica column chromatog-
raphy.
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Procedure for the Synthesis of 6a
Ethyl 2-diazo-3-oxobutanoate 3b (1.56 g, 10.0 mmol), eth-
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Procedure for the Recycling of the Catalyst
To test the recyclability of the HCP–PPh3–Ru catalyst, the
mixture of the reaction system was filtered at the end of the
reaction. The obtained solid catalyst was washed with etha-
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for the reuse of the catalyst in the other reactions is similar
to this method.
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