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Synlett 2019; 30(19): 2198-2202
DOI: 10.1055/s-0039-1690228
letter
© Georg Thieme Verlag Stuttgart · New York

Catalytic Asymmetric Synthesis of Atropisomeric Quinolines through the Friedländer Reaction

Junlin Wan
a   College of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China   Email: junjiang@wzu.edu.cn
,
Hongxin Liu
a   College of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China   Email: junjiang@wzu.edu.cn
b   Institute of New Materials and Industrial Technology, Wenzhou University, Wenzhou, 325035, P. R. of China
,
Yunjun Lan†
a   College of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China   Email: junjiang@wzu.edu.cn
,
Xinhua Li
a   College of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China   Email: junjiang@wzu.edu.cn
,
Xingena Hu
a   College of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China   Email: junjiang@wzu.edu.cn
,
Juan Li
a   College of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China   Email: junjiang@wzu.edu.cn
,
Hong-Ping Xiao
a   College of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China   Email: junjiang@wzu.edu.cn
,
Jun Jiang  ∗
a   College of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China   Email: junjiang@wzu.edu.cn
› Author AffiliationsWe are grateful for financial support from the National Natural Science Foundation of China (NSFC, Grant Nos. 21573161 and 21571144), the Natural Science Foundation of Zhejiang Province (Grant Nos. LY18B020011 and LQ19B020004), and the Foundation of Wenzhou Basic Scientific Research Project (G20180015).
Further Information

Publication History

Received: 05 October 2019

Accepted after revision: 13 October 2019

Publication Date:
05 November 2019 (online)

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Abstract

A phosphoric acid catalyzed atroposelective Friedländer reaction was developed in which acetylacetone and a variety of 2′-substituted 2-aminobenzophenones were successfully employed to give optically active biaryl quinolines in good yields and with high enantioselectivities.

Key words

Friedländer reaction - atroposelectivity - quinolines - phosphoric acids - acetylacetone

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690228.
  • Supporting Information
 

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  • 15 Phosphoric-Acid-Catalyzed Asymmetric Friedländer Reaction; General Procedure A Schlenk tube was charged with the appropriate 2-aminobenzophenone 1 (1 equiv, 0.1 mmol), acetylacetone (2; 5 equiv, 0.5 mmol), catalyst Cat.5 (0.1 equiv, 10% mmol), powdered 5 Å MS (50 mg), and anhyd PhCN (0.5 mL). The resulting mixture was stirred at rt for 12 h and then at 120 °С for an additional 8 h. When the reaction was complete, the mixture was purified by flash column chromatography [silica gel, PE–EtOAc (8:1 to 6:1)]. 1-[2-Methyl-5-(3-{2-[4-(trifluoromethyl)phenyl]ethyl}phenyl)quinolin-3-yl]ethanone (4a) Yellow liquid; yield: 39.9 mg (92%; ee 88%); [α]D 27 +5.6 (c 0.01, EtOAc). HPCL [Daicel Chiralpak AD-H, hexane–i-PrOH (98:2), flow rate: 0.7 mL/min, λ = 254 nm, 25°С]: t R (major) = 11.40 min; t R (minor) = 12.42 min. 1H NMR (500 MHz, CDCl3): δ = 8.09 (d, J = 8.4 Hz, 1 H), 7.76–7.68 (m, 1 H), 7.46 (t, J = 7.3 Hz, 1 H), 7.42–7.32 (m, 5 H), 7.25 (d, J = 9.4 Hz, 1 H), 7.19 (d, J = 7.4 Hz, 1 H), 6.89 (d, J = 8.0 Hz, 2 H), 2.81–2.60 (m, 2 H), 2.71 (s, 3 H), 2.66–2.60 (m, 1 H), 2.56–2.49 (m, 1 H), 2.08 (s, 3 H). 13C NMR (126 MHz, CDCl3): δ = 205.01, 153.54, 147.37, 145.26, 143.11, 139.86, 135.16, 134.42, 130.22, 130.08, 129.38, 129.28, 128.93, 128.53, 126.62, 126.23, 125.98, 125.46, 125.20, 125.17, 125.14, 125.11, 36.10, 34.64, 31.90, 23.85. HRMS (Bruker micrOTOF-QII): m/z [M + H]+ calcd for C27H23F3NO: 434.1726; found: 434.1743.1-[2,7-Dimethyl-5-(3-{2-[4-(trifluoromethyl)phenyl]ethyl}phenyl)quinolin-3-yl]ethanone (4b) Yellow liquid; yield: 38.9 mg (87%; ee 93%); [α]D 27 +16.4 (c 0.01, EtOAc); HPLC [Daicel Chiralpak AD-H, hexane–i-PrOH (98:2), flow rate 0.7 mL/min, λ = 254 nm, 25 °С]: t R (major) = 9.18 min, t R (minor) = 11.06 min. 1H NMR (500 MHz, CDCl3): δ = 7.86 (s, 1 H), 7.45 (t, J = 7.5 Hz, 1 H), 7.40 (d, J = 7.4 Hz, 1 H), 7.35–7.31 (m, 3 H), 7.18 (t, J = 7.6 Hz, 2 H), 7.12 (d, J = 8.5 Hz, 1 H), 6.89 (d, J = 8.0 Hz, 2 H), 2.81–2.71 (m, 2 H), 2.69 (s, 3 H), 2.66–2.60 (m, 1 H), 2.58–2.51 (m, 1 H), 2.54 (s, 3 H), 2.07 (s, 3 H). 13C NMR (126 MHz, CDCl3): δ = 205.21, 153.48, 147.61, 145.30, 142.95, 140.73, 139.81, 134.64, 134.42, 130.06, 129.38, 129.19, 128.84, 128.56, 127.98, 126.19, 125.66, 125.17, 125.14, 125.11, 125.08, 123.42, 36.13, 34.62, 31.96, 23.85, 21.71. HRMS (Bruker micrOTOF-QII): m/z [M + H]+ calcd for C28H25F3NO: 448.1883; found: 448.1879.
  • 16 CCDC 1957624 contains the supplementary crystallographic data for compound (S,R)-5. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.