| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345987 | Tetrahedron: Asymmetry | 2012 | 6 Pages |
In the presence of an (R)-MOP-Pd2(dba)3 catalyst, the reaction of ortho-tert-butylaniline with 2-bromophenyl arylethynyl ketone proceeded via a tandem amination (1,4-addition of aniline to an ynone and subsequent intramolecular Buchwald–Hartwig amination) to afford axially chiral N-(2-tert-butylphenyl)-2-aryl-4-quinolinone derivatives with moderate enantioselectivity (up to 72% ee).
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1-(2-tert-Butylphenyl)-2-phenylquinolin-4(1H)-oneC25H23NOee = 57% by HPLC analysis using OD-3 column[α]D25=-36.1 (c 0.41, CHCl3)Source of chirality: chiral catalystAbsolute configuration: nd
1-(2-Isopropylphenyl)-2-phenylquinolin-4(1H)-oneC24H21NOee = 30% by HPLC analysis using OD-3 column[α]D25=-29.9 (c 0.40, CHCl3)Source of chirality: chiral catalystAbsolute configuration: nd
1-(2,5-Di-tert-butylphenyl)-2-phenylquinolin-4(1H)-oneC29H31NOee = 21% by HPLC analysis using OD-3 column[α]D25=-14.9 (c 0.40, CHCl3)Source of chirality: chiral catalystAbsolute configuration: nd
1-(2-(tert-Butyl)phenyl)-2-(4-methoxyphenyl)quinolin-4(1H)-oneC26H25NO2ee = 52% by HPLC analysis using OD-3 column[α]D25=-42.3 (c 0.41, CHCl3)Source of chirality: chiral catalystAbsolute configuration: nd
1-(2-(tert-Butyl)phenyl)-2-(p-tolyl)quinolin-4(1H)-oneC26H25NOee = 55% by HPLC analysis using OD-3 column[α]D25=-35.1 (c 0.42, CHCl3)Source of chirality: chiral catalystAbsolute configuration: nd
1-(2-(tert-Butyl)phenyl)-2-(4-chlorophenyl)quinolin-4(1H)-oneC25H22ClNOee = 66% by HPLC analysis using OD-3 column[α]D25=-38.3 (c 0.41, CHCl3)Source of chirality: chiral catalystAbsolute configuration: nd
1-(2-(tert-Butyl)phenyl)-2-(4-nitrophenyl)quinolin-4(1H)-oneC25H22N2O3ee = 72% by HPLC analysis using OD-3 column[α]D25=-49.1 (c 0.40, CHCl3)Source of chirality: chiral catalystAbsolute configuration: (S)
1-(2-(tert-Butyl)phenyl)-2-(2-methoxyphenyl)quinolin-4(1H)-oneC26H25NO2ee = 60% by HPLC analysis using AD column[α]D25=+19.4 (c 0.40, CHCl3)Source of chirality: chiral catalystAbsolute configuration: nd
