| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347143 | Tetrahedron: Asymmetry | 2009 | 5 Pages |
Using Schiff-base amino alcohols as catalysts which were readily derived from natural amino acids in three steps, a series of valuable optically active thiophenyl methanols (4a–4n) were first obtained in good yields and high enantioselectivities (up to 96% ee) through the asymmetric addition of thiophenylboronic acid to aldehydes in the presence of ZnEt2 in toluene.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(Phenyl)-(2′-thienyl)methanolC11H10OSEe = 93%[α]D20=-3.6 (c 1.89, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: unknown
(2-Chlorophenyl)-(2′-thienyl)methanolC11H9ClOSEe = 92%[α]D20=-31 (c 1.1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: unknown
(3-Chlorophenyl)-(2′-thienyl)methanolC11H9ClOSEe = 81%[α]D20=-13 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: unknown
(4-Chlorophenyl)-(2′-thienyl)methanolC11H9ClOSEe = 85%[α]D20=-19 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: unknown
(4-Fluorophenyl)-(2′-thienyl)methanolC11H9FOSEe = 92%[α]D20=-15 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: unknown
(2-Methylphenyl)-(2′-thienyl)methanolC12H12OSEe = 94%[α]D20=-24 (c 1.3, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: unknown
(R)-(4-Methylphenyl)-(2′-thienyl)methanolC12H12OSEe = 84%[α]D20=-16 (c 1.0, CHCl3)
(2-Methoxyphenyl)-(2′-thienyl)methanolC12H12O2SEe = 95%[α]D20=-20 (c 0.95, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: unknown
(3-Methoxyphenyl)-(2′-thienyl)methanolC12H12O2SEe = 93%[α]D20=-10 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: unknown
(4-Methoxyphenyl)-(2′-thienyl)methanolC12H12O2SEe = 96%[α]D20=-16 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: unknown
(2-Bromophenyl)-(2′-thienyl)methanolC11H9BrOSEe = 95%[α]D20=-49 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: unknown
(4-Bromophenyl)-(2′-thienyl)methanolC11H9BrOSEe = 92%[α]D20=-17 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: unknown
(2-Naphthyl)-(2′-thienyl)methanolC15H12OSEe = 88%[α]D20=-57 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: unknown
(2-Furanyl)-(2′-thienyl)methanolC9H8O2SEe = 82%[α]D20=-11 (c 1.7, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: unknown
