| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1349008 | Tetrahedron: Asymmetry | 2010 | 11 Pages |
Over 20 new and easily prepared diamines were screened for the asymmetric Morita–Baylis–Hillman reaction. Chiral non-racemic 3-(N,N-dimethylamino)-1-methylpyrrolidine was found to promote efficiently the reaction of methyl vinyl ketone and substituted benzaldehydes. Enantiomeric excesses up to 73% were reached with electron-deficient benzaldehyde derivatives. After a simple deprotonation, one of these diamines was transformed into a chiral mixed aggregate for the enantioselective synthesis of (R)-1-o-tolylethanol with 76% ee.
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Dimethyl-((R)-1-methylpyrrolidin-3-yl)amineC7H16N2[α]D20=-0.4 (c 0.80, CHCl3)Source of chirality: (R)-1-benzyl-3-amino-pyrrolidineAbsolute configuration: (3R)
((R)-1-Benzylpyrrolidin-3-yl)dimethylamineC13H20N2[α]D20=+2.8 (c 0.50, CHCl3)Source of chirality: (R)-1-benzyl-3-amino-pyrrolidineAbsolute configuration: (3R)
(R)-1′-Methyl-[1,3′]bipyrrolidineC9H18N2[α]D20=-6.5 (c 1.20, CHCl3)Source of chirality: (R)-1-benzyl-3-amino-pyrrolidineAbsolute configuration: (3R)
(S)-N-Benzyl-N-methyl-N-1-methylpyrrolidin-3-yl)amineC13H20N2[α]D20=+5.5 (c 1.0, CHCl3)Source of chirality: (S)-1-benzyl-3-amino-pyrrolidineAbsolute configuration: (3S)
2-[(S)-3-Dimethylaminopyrrolydin-1-ylmethyl]phenolC13H20N2O[α]D20=+16.6 (c 2.5, CHCl3)Source of chirality: (S)-1-benzyl-3-amino-pyrrolidineAbsolute configuration: (3S)
3-[(S)-3-Dimethylaminopyrrolydin-1-ylmethyl]phenolC13H20N2O[α]D20=+1.2 (c 0.9, CHCl3)Source of chirality: (S)-1-benzyl-3-amino-pyrrolidineAbsolute configuration: (3S)
(R)-N2,N2,N3,N3-Tetramethylpyrrolidine-1,3-diamineC8H19N3[α]D20=+7.1 (c 0.5, CHCl3)Source of chirality: (R)-1-benzyl-3-amino-pyrrolidineAbsolute configuration: (3R)
2-{[Methyl-((S)-1-methylpyrrolidin-3-yl)amino)]methyl}phenolC13H20N2O[α]D20=-9.5 (c 1.0, CHCl3)Source of chirality: (S)-1-benzyl-3-amino-pyrrolidineAbsolute configuration: (3S)
(S)-1-Benzyl-N-[(R)-2,2,2-trifluoro-1-phenylethyl]pyrrolidin-3-amineC19H21F3N2[α]D20=-67 (c 7.0, CH2Cl2)Source of chirality: (S)-1-benzyl-3-amino-pyrrolidineAbsolute configuration: (3S, 1′R)
