| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347134 | Tetrahedron: Asymmetry | 2009 | 4 Pages |
The copper(I)-catalyzed enantioselective alkynylation of aldimines incorporating a 2,3,4,6-tetrakis-O-pivaloyl-d-glucopyranosyl (Piv4Glc) chiral auxiliary with terminal alkynes is reported. The present system provides a versatile tool for the construction of optically active propargylamine derivatives. Good yields and enantiomeric excess values were achieved with an array of imines and biologically active, propargylamine derivatives.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1,3-diphenylprop-2-ynylamineC41H55NO9De = 90%[α]D20=+30.55 (c 0.036, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)
N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(4-nitrophenyl)-3-phenylprop-2-ynylamineC41H54N2O11De = 91%[α]D20=+32.4 (c 0.032, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)
N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(4-chlorophenyl)-3-phenylprop-2-ynylamineC41H54ClNO9De = 93%[α]D20=+36.6 (c 0.023, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)
N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(3-trifluoromethyl)penyl-3-phenylprop-2-ynylamineC41H54N2O11De = 96%[α]D20=+16.9 (c 0.043, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)
N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(4-trifluoromethyl)penyl-3-phenylprop-2-ynylamineC42H54F3NO9De = 93%[α]D20=+31.45 (c 0.027, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)
N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(4-methylphenyl)-3-phenylprop-2-ynylamineC42H57NO9De = 92%[α]D20=+17.2 (c 0.073, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)
N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(4- chlorophenyl)-hept-2-ynylamineC39H58ClNO9De = 78%[α]D20=+11.9 (c 0.056, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)
N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(4-chlorophenyl)-3-(trimethylsilyl)-prop-2-ynylamineC38H58ClNO9SiDe = 28%[α]D20=+9.4 (c 0.039, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)
