Advanced Synthesis & Catalysis
10.1002/adsc.201900218
1
. Procedure for the synthesis of the racemate of References
3
aa
To a dried small bottle were added 2a (0.05
mmol), cat. (4.0 mg, 0.01 mmol) and 0.5 mL CH Cl
[
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2
2
.
The mixture was stirred at room temperature for 5
min, and 1a was then added. After stirring at room
temperature for 5 h, the reaction mixture was
concentrated and directly purified by silica gel
column chromatography to afford the racemates of
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3
2
aa.
. Procedure of asymmetric Michael/Mannich
cascade reactions for the synthesis of 3aa
To a dried small bottle were added 2a (0.1 mmol)
and catalyst C6 (3.6 mg, 0.005 mmol, 5 mol %) in
CH Cl (0.5 mL). The mixture was stirred at room
temperature for 5 min, and 1a (0.105 mmol) was then
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added. After stirring at room temperature for 5 h, the
2
a was completely consumped as detected by TLC
1
67–168; e) L.-Q. Lu, J.-R. Chen, W.-J. Xiao, Acc.
analysis (petroleum ether/EtOAc 5:1). After that, the
reaction mixture was concentrated and directly
purified by silica gel column chromatography to
afford the desired product 3aa.
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3
. Procedure of sequential cascade reactions for
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the synthesis of racemate of 5
1
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mmol), cat. (4.0 mg, 0.01 mmol) and 0.5 mL CH
2
Cl .
2
The mixture was stirred at room temperature for 5
min, and 1ar (0.055 mmol) was then added. After
stirring at room temperature for 24 h and 2aj were
completely consumped as detected by TLC analysis,
4ae (0.06 mmol) were added. After stirring at room
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temperature for another 12 h, the reaction mixture
was concentrated and directly purified by silica gel
column chromatography (petroleum ether/EtOAc 2:1
to 1:1) to afford the racemates of 5aaa5aje.
2
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4
. Procedure of asymmetric sequential cascade
reactions for the synthesis of 5
To a dried small bottle were added 2aj (0.1
mmol) and catalyst C6 (7.2 mg, 0.01 mmol, 10
mol %) and 0.5 mL CH
2
Cl . The mixture was stirred
2
at room temperature for 5 min, and 1ar (0.105
mmol) was then added. After stirring at room
temperature for 24 h and 2aj were completely
consumped as detected by TLC analysis, 4ae (0.12
mmol) were added. After stirring at room temperature
for another 12 h, the reaction mixture was
concentrated and directly purified by silica gel
column chromatography (petroleum ether/EtOAc 2:1
to 1:1) to afford the desired product 5.
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Acknowledgements
We are grateful for financial support from the National
Post-doctoral Program for Innovative Talents of China (No.
BX201700030) and the project funded by China
Postdoctoral Science Foundation (No. 2017M620630). We
also thank the Analysis & Testing Center of Beijing Institute
of Technology.
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7
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