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COMMUNICATION
Journal Name
information). The enamine attacked the carbon atom of the
R)-2-aryl-2,3-
DOI: 10.1039/C6RA01247G
C=N on Re face, leading to the formation of (
dihydro-4-quinolone.
Z. Cao, Y. Niu, X. Zhao, J. Zhou. Acta Chim. Sinica 2014, 72
867.
,
5
6
(a) R. Shintani, T. Yamaguchi, T. Kimura, T. Hayashi, Org. Lett.
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7
Conclusions
In summary, we have developed
organocatalytic one-pot synthesis of ( )-2-aryl-2,3-dihydro-4-
quinolones from -aminoacetophenones and aryl aldehydes.
a highly efficient
R
L. You, Heterocycles 2010, 80, 765; (c) X. Liu, Y. Lu, Org. Lett
2010, 12, 5592; (d) X. Xiao, X. Liu, S. Dong, Y. Cai, L. Lin, X.
Feng, Chem. Eur. J. 2012, 18 15922; (e) S. Cheng, L. Zhao, S.
.
o
The products were obtained in good yields up to 99% ee.
Compared to previous approaches, the approach was
characterized by metal free, solvent free and protecting group
free. Preliminary mechanistic study showed that the protocol
probably underwent an asymmetric Mannich process. Due to
easy operation and high efficiency, this method would be
prospective in the synthesis of bioactive 2-aryl-2,3-dihydro-4-
quinolones, thereby facilitating biological and medicinal
chemistry studies of such compounds.
,
Yu, Adv. Synth. Catal. 2014, 356, 982.
7
(a) K. Kanagaraj, K. Pitchumani, J. Org. Chem. 2013, 78, 744;
(b) For recent elegant one-pot asymmetric synthesis, see: X.-
P. Yin, X.-P. Zeng, Y.-L. Liu, F.-M. Liao, J.-S. Yu, F. Zhou, J.
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8
9
Acknowledgements
10 Y.-L. Zhang, Y.-Q. Wang, Tetrahedron Lett. 2014, 55, 3255.
This research was supported by National Natural Science
Foundation of China (NSFC-20972126, 21272185), the Program
for New Century Excellent Talents in University of the Ministry
of Education China (NCET-10-0937).
Notes and references
†
General procedure for 2-Aryl-2,3-dihydro-4-quinolones synthesis: To a 1.5 mL
test tube were added 0.01mmol (10 mmol%) of organocatalyst 4a, 0.1 mmol of
2’-hydroxyacetophenones and 0.1 mmol of aryl aldehydes . Then the reaction
1
2
mixture was left at room temperature for sufficient time (based on monitoring
by thin-layer chromatography), and finally purified by column chromatography
with 10% EtOAc / hexanes as eluent to give the products 3.
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