10.1002/adsc.201601423
Advanced Synthesis & Catalysis
derivatives. This method offers a approach to C(sp3)–
C(sp3) bond conncetion from ainert methyl group
through a redox-neutral mechanism. A wide range of
substituted 2-methylquinoline-3-carbaldehydes and
1,2,3,4-tetrahydroisoquinolines can be applied for
this reaction with good to excellent yields (up to
99%). The annulation products, which have similar
structures to those of natural THPBs, can be used for
biological studies. Further exploration of this method
for new organic transformations and the use of this
methodology in the synthesis of biologically relevant
molecules are under investigation in our laboratories.
Wang, X. Liu, W. Liu, W. Kang, J. Zhou, J. Zeng, Nat.
Prod. Res. 2014, 28, 413-419.
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General Procedure for the Synthesis of Compounds 3
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A mixture of 1a (0.1 mmol) and Al(OTf)3 (0.03 mmol)
was stirred in the toluene (1.5 mL) for 30 min under N2 at
room temperature. Then 3 Å MS (50 mg) and a secondary
amine 2a (0.13 mmol) were added. The mixture was stirred
o
at 80 C. After the reaction was completed (monitored
using TLC), the mixture was cooled to room temperature
and filtered, the residue was washed with DCM. The
combined organic phases were combined and the solvent
was evaporated. The residue was purified by column
chromatography (neutral alumina) to give the
corresponding product 3a.
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Acknowledgements
Financial support of this research from the program for the
National Science Foundation of China (21372073, 21572054 and
21572055), the Fundamental Research Funds for the Central
Universities and East China University of Science and
Technology, and the China 111 Project
acknowledged.
is gratefully
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