Catalytic Asymmetric Synthesis of Atropisomeric Quinolines through the Friedländer Reaction

Junlin Wan; Hongxin Liu; Yunjun Lan; Xinhua Li; Xingena Hu; Juan Li; Hong-Ping Xiao; Jun Jiang

doi:10.1055/s-0039-1690228

Synlett, Table of Contents

Synlett 2019; 30(19): 2198-2202
DOI: 10.1055/s-0039-1690228

letter

Catalytic Asymmetric Synthesis of Atropisomeric Quinolines through the Friedländer Reaction

Junlin Wan

^aCollege of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China Email: junjiang@wzu.edu.cn

,

Hongxin Liu

^aCollege of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China Email: junjiang@wzu.edu.cn

^bInstitute of New Materials and Industrial Technology, Wenzhou University, Wenzhou, 325035, P. R. of China

,

Yunjun Lan†

^aCollege of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China Email: junjiang@wzu.edu.cn

,

Xinhua Li

^aCollege of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China Email: junjiang@wzu.edu.cn

,

Xingena Hu

^aCollege of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China Email: junjiang@wzu.edu.cn

,

Juan Li

^aCollege of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China Email: junjiang@wzu.edu.cn

,

Hong-Ping Xiao

^aCollege of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China Email: junjiang@wzu.edu.cn

,

Jun Jiang ∗

^aCollege of Chemistry and Materials Engineering,Wenzhou University, Wenzhou, Zhejiang Province 325035, P. R. of China Email: junjiang@wzu.edu.cn

› Author Affiliations

Abstract

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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

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References

References and Notes
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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.

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