| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1350273 | Tetrahedron: Asymmetry | 2008 | 6 Pages |
New optically active aminonaphthols were obtained by condensation of 2-naphthol, benzaldehyde and (R)-(+)-1-(1-naphthyl)ethylamine or (R)-(+)-1-(2-naphthyl)ethylamine. Their N-methylated derivatives were also synthesized. The new aminonaphthols 2, 4, 5 and 7 were found to catalyze the enantioselective ethylation of aryl aldehydes to 1-aryl-1-propanols (up to 92% ee). The reactions were accelerated greatly by microwave irradiation.
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1-[(R)-Phenyl-1′(R)-(1-naphthyl)ethylaminomethyl]-2-naphtholC29H25NOEe = >99%[α]D20=-351.5 (c 0.5, CHCl3)Source of chirality: (R)-(+)-1-(1-naphthyl)ethylamineAbsolute configuration: (1R,1′R)
(1R)-1-Phenyl-2-[(1′R)-1′-(1-naphthylethyl)]-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazineC30H25NOEe = >99%[α]D20=-218.3 (c 0.5, CHCl3)Source of chirality: 1-[(R)-phenyl-1′(R)-(1-naphthyl)ethylaminomethyl]-2-naphtholAbsolute configuration: (1R,1′R)
N-Methyl-1-[(R)-Phenyl-1′(R)-(1-naphthyl)ethylaminomethyl]-2-naphtholC30H27NOEe = >99%[α]D20=-399.4 (c 0.5, CHCl3)Source of chirality: (1R)-1-phenyl-2-[(1′R)-1′-(1-naphthylethyl)]-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazineAbsolute configuration: (1R,1′R)
1-[(R)-Phenyl-1′(R)-(2-naphthyl)ethylaminomethyl]-2-naphtholC29H25NOEe = >99%[α]D20=-236.0 (c 0.5, CHCl3)Source of chirality: (R)-(+)-1-(2-naphthyl)ethylamineAbsolute configuration: (1R,1′R)
(1R)-1-Phenyl-2-[(1′R)-1′-(2-naphthylethyl)]-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazineC30H25NOEe = >99%[α]D20=-143.0 (c 0.5, CHCl3)Source of chirality: 1-[(R)-phenyl-1′(R)-(2-naphthyl)ethylaminomethyl]-2-naphtholAbsolute configuration: (1R,1′R)
N-Methyl-1-[(R)-Phenyl-1′(R)-(2-naphthyl)ethylaminomethyl]-2-naphtholC30H27NOEe = >99%[α]D20=-255.0 (c 0.5, CHCl3)Source of chirality: (1R)-1-phenyl-2-[(1′R)-1′-(2-naphthylethyl)]-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazineAbsolute configuration: (1R,1′R)
