Organic Letters
Letter
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construction but also provides a useful avenue to access axially
chiral polysubstituted 4-arylquinoline scaffolds which might be
of significance for future biological and medicinal studies.
ASSOCIATED CONTENT
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(6) Li, L.; Seidel, D. Catalytic Enantioselective Friedlander
S
* Supporting Information
Condensations: Facile Access to Quinolines with Remote Stereogenic
Centers. Org. Lett. 2010, 12, 5064−5067.
(7) Ren, L.; Lei, T.; Gong, L.-Z. Brønsted acid-catalyzed
The Supporting Information is available free of charge on the
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enantioselective Friedlander condensations: achiral amine promoter
plays crucial role in the stereocontrol. Chem. Commun. 2011, 47,
11683−11685.
Experimental procedures, NMR spectra, HPLC traces,
X-ray and analytical data (PDF)
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(8) Banon-Caballero, A.; Guillena, G.; Najera, C. Solvent-Free
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Enantioselective Friedlander Condensation with Wet 1,1’-Binaph-
thalene-2,2’-diamine-Derived Prolinamides as Organocatalysts. J. Org.
Chem. 2013, 78, 5349−5356.
Accession Codes
CCDC 1906249 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
(9) For some reviews: (a) Kozlowski, M. C.; Morgan, B. J.; Linton,
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(10) For reviews: (a) Clayden, J.; Moran, W. J.; Edwards, P. J.;
Laplante, S. R. The Challenge of Atropisomerism in Drug Discovery.
Angew. Chem., Int. Ed. 2009, 48, 6398−6401. (b) Smyth, J. E.; Butler,
N. M.; Keller, P. A. A twist of nature-the significance of atropisomers
in biological systems. Nat. Prod. Rep. 2015, 32, 1562−1583. (c) Zask,
A.; Murphy, J.; Ellestad, G. A. Biological Stereoselectivity of
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AUTHOR INFORMATION
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Corresponding Author
ORCID
Notes
(11) (a) Bringmann, G.; Price Mortimer, A. J.; Keller, P. A.; Gresser,
M. J.; Garner, J.; Breuning, M. Atroposelective Synthesis of Axially
Chiral Biaryl Compounds. Angew. Chem., Int. Ed. 2005, 44, 5384−
5427. (b) Kumarasamy, E.; Raghunathan, R.; Sibi, M. P.; Sivaguru, J.
Nonbiaryl and Heterobiaryl Atropisomers: Molecular Templates with
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2015, 115, 11239−11300. (c) Wallace, T. W. Biaryl synthesis with
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(d) Zhang, D.; Wang, Q. Palladium catalyzed asymmetric Suzuki-
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ligands and recent advances. Coord. Chem. Rev. 2015, 286, 1−16.
(e) Wencel-Delord, J.; Panossian, A.; Leroux, F. R.; Colobert, F.
Recent advances and new concepts for the synthesis of axially
stereoenriched biaryls. Chem. Soc. Rev. 2015, 44, 3418−3430.
(f) Baudoin, O. The Asymmetric Suzuki Coupling Route to Axially
Chiral Biaryls. Eur. J. Org. Chem. 2005, 2005, 4223−4229. (g) Li, Y.-
M.; Kwong, F.-Y.; Yu, W.-Y.; Chan, A. S. C. Recent advances in
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catalysis. Coord. Chem. Rev. 2007, 251, 2119−2144. (h) Renzi, P.
Organocatalytic synthesis of axially chiral atropisomers. Org. Biomol.
Chem. 2017, 15, 4506−4516. (i) Loxq, P.; Manoury, E.; Poli, R.;
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Catalyst-Controlled Stereoselective Synthesis of Atropisomers. ACS
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The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We are thankful for the financial support from the National
Natural Science Foundation of China (Nos. 21602097 and
21601006).
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