A common heterocyclic compound, the chiral-catalyst compound, name is [1,1′-Binaphthalene]-2,2′-diamine,cas is 4488-22-6, mainly used in chemical industry, its synthesis route is as follows.,4488-22-6
To a solution of 2 (1.421 g, 5 mmol) in benzene (5 mL) was added allylalcohol (0.850 mL, 12.5 mmol) and dried molsieve (1 g, 4 A) and the mixture was degassed. Subsequently, Ti(i-OPr)4, (710 mg, 740 muL, 2.5 mmol), PPh3 (105 mg, 0.4 mmol), and Pd(OAc)2 (22.5 mg, 0.1 mmol) was added and the reaction was stirred under Ar at 50 C. The conversion was monitored by TLC. After extractive work-up with DCM/water, drying (MgSO4), and evaporation, the crude product was purified by chromatography in EtOAc (5?20%)/heptane to afford 1.55 g (85%) of 6 as a slightly brown crystaline solid; m.p.: 95-99 C. 1H-NMR delta = 7.87 (d, J = 9.0 Hz, 2H); 7.78 (dm, J = 7.7 Hz, 2H); 7.21 (d, J = 9.1 Hz, 2H); 7.14-7.22 (m, 4H); 6.99 (dm, J = 7.9 Hz, 2H); 5.77 (ddm, J = 17.3, 10.3 Hz, 2H); 5.12 (dm, J = 17.3 Hz, 2H); 5.02 (dm, J = 10.3 Hz, 2H); 3.92 (br.s, 2H); 3.77-3.86 (br.m, 4H). 13C-NMR delta = 144.2 (C); 135.7 (CH); 133.9 (C); 129.5 (CH); 128.1 (CH); 127.7 (C); 126.7 (CH); 123.9 (CH); 122.0 (CH); 115.6 (CH2); 114.2 (CH); 112.0 (C); 46.1 (CH2). HRMS calcd for C26H25N2 [M + H]+: 365.2018; found: 365.2011.
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Reference£º
Article; Lemmerer, Miran; Abraham, Michael; Brutiu, Bogdan R.; Roller, Alexander; Widhalm, Michael; Molecules; vol. 24; 17; (2019);,
Chiral Catalysts
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