| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348280 | Tetrahedron: Asymmetry | 2007 | 6 Pages |
The 1,3-aminophenol ligand (R)-1 was found to be a good catalyst for the zinc phenylacetylene addition to aldehydes. The high activity and enantioselectivity could be improved upon by basic additives. The enantioselectivity follows a linear free energy relationship with higher enantioselectivity obtained for the more reactive aryl aldehydes.
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(R)-1,3-Diphenyl-prop-2-yn-1-olC15H12OEe = 69%[α]D23=+3.2 (c 0.668, DCM)Source of chirality: alkynylationAbsolute configuration: (R)
(R)-1-(4-Nitrophenyl)-3-phenyl-prop-2-yn-1-olC15H11NO3Ee = 99%[α]D23=+13.3 (c 0.15, DCM)Source of chirality: alkynylationAbsolute configuration: (R)
(+)-1-(3-Nitrophenyl)-3-phenyl-prop-2-yn-1-olC15H11NO3Ee = 99%[α]D23=+9.4 (c 0.276, DCM)
(−)-1-(2-Nitrophenyl)-3-phenyl-prop-2-yn-1-olC15H11NO3Ee = 36%[α]D23=-2.9 (c 0.34, DCM)
(R)-1-(4-Methylphenyl)-3-phenyl-prop-2-yn-1-olC16H14OEe = 60%[α]D23=+2.2 (c 0.452, DCM)Source of chirality: alkynylationAbsolute configuration: (R)
(R)-1-(3-Methylphenyl)-3-phenyl-prop-2-yn-1-olC16H14OEe = 66%[α]D23=+2.8 (c 0.36, DCM)Source of chirality: alkynylationAbsolute configuration: (R)
(R)-1-(2-Methylphenyl)-3-phenyl-prop-2-yn-1-olC16H14OEe = 12%[α]D23=-3.6 (c 0.436, DCM)Source of chirality: alkynylationAbsolute configuration: (R)
(R)-1-(4-Chlorophenyl)-3-phenyl-prop-2-yn-1-olC15H11ClOEe = 88%[α]D23=+8.5 (c 0.4, DCM)Source of chirality: alkynylationAbsolute configuration: (R)
(R)-1-(3-Chlorophenyl)-3-phenyl-prop-2-yn-1-olC15H11ClOEe = 89%[α]D23=+9.8 (c 0.408, DCM)Source of chirality: alkynylationAbsolute configuration: (R)
(−)-1-(2-Chlorophenyl)-3-phenyl-prop-2-yn-1-olC15H11ClOEe = 88%[α]D23=-31.9 (c 0.514, DCM)
(R)-1-(4-Bromophenyl)-3-phenyl-prop-2-yn-1-olC15H11BrOEe = 89%[α]D23=+3.9 (c 0.568, DCM)Source of chirality: alkynylationAbsolute configuration: (R)
(R)-1-(4-Methoxyphenyl)-3-phenyl-prop-2-yn-1-olC16H14O2Ee = 56%[α]D23=+0.9 (c 0.442, DCM)Source of chirality: alkynylationAbsolute configuration: (R)
(R)-1,5-Diphenyl-pent-1-yn-3-olC17H16O2Ee = 22%[α]D23=-13.9 (c 0.458, CHCl3)Source of chirality: alkynylationAbsolute configuration: (R)
(+)-1,4-Diphenyl-pent-1-yn-3-olC17H16OEe = 20%[α]D23=+15.5 (c 1.21, CHCl3)
(+)-1,5-Diphenyl-pent-1-en-4-yn-3-olC17H14OEe = 36%[α]D23=+0.7 (c 0.722, CHCl3)
(R)-2,4-Di-tert-butyl-6-(2,2-dimethyl-1-(methylamino)propyl)phenolC20H35NOEe >99%[α]D20=-31.7 (c 0.328, CH3COOCH2CH3)Source of chirality: (R)-2-(1-amino-2,2-dimethylpropyl)-4,6-di-tert-butylphenolAbsolute configuration: (R)
