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1 article(s) from Alpagut, Y

Control of asymmetric biaryl conformations with terpenol moieties: Syntheses, structures and energetics of new enantiopure C₂-symmetric diols

Y. Alpagut,
B. Goldfuss and
J.-M. Neudörfl

Beilstein J. Org. Chem. 2008, 4, No. 25, doi:10.3762/bjoc.4.25

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Graphical Abstract

Scheme 1: Atropisomeric BINOL and conformationally restricted, (−)-fenchone-based (M)-BIFOL.

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Scheme 2: Syntheses of (M)-BIMOL, (P)-BIVOL, (P)-BICOL, and (P)-BIMEOL.

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Figure 1: X-Ray crystal structure of (M)-BIMOL. An acetone molecule, binding to the external OH group, is omi...

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Figure 2: X-Ray crystal structure of (P)-BIVOL. A water molecule, binding to the external OH group, is omitte...

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Figure 3: X-Ray crystal structure of (P)-BICOL. A water molecule, binding to the external OH group, is omitte...

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Figure 4: X-Ray crystal structure of (P)-BIMEOL. An ethanol molecule, binding to the external OH group, is om...

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Figure 5: B3LYP/6-31++G**:AM1 optimized structure of (M)-BIMOL, E_rel. = 0.0 kcal/mol.

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Figure 6: B3LYP/6-31++G**:AM1 optimized structure of (P)-BIMOL, E_rel. = 1.3 kcal/mol.

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Figure 7: B3LYP/6-31++G**:AM1 optimized structure of (M)-BIVOL, E_rel. = 5.1 kcal/mol.

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Figure 8: B3LYP/6-31++G**:AM1 optimized structure of (P)-BIVOL, E_rel. = 0.0 kcal/mol.

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Figure 9: B3LYP/6-31++G**:AM1 optimized structure of (M)-BICOL, E_rel. = 5.8 kcal/mol.

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Figure 10: B3LYP/6-31++G**:AM1 optimized structure of (P)-BICOL, E_rel. = 0.0 kcal/mol.

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Figure 11: B3LYP/6-31++G**:AM1 optimized structure of (M)-BIMEOL, E_rel. = 5.4 kcal/mol.

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Figure 12: B3LYP/6-31++G**:AM1 optimized structure of (P)-BIMEOL, E_rel. = 0.0 kcal/mol.

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Scheme 3: Co-solvent adducts in the X-ray structures of (M)-BIMOL, (P)-BIVOL, (P)-BICOL, and (P)-BIMEOL.

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Full Research Paper

Published 10 Jul 2008

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Control of asymmetric biaryl conformations with terpenol moieties: Syntheses, structures and energetics of new enantiopure C2-symmetric diols

Control of asymmetric biaryl conformations with terpenol moieties: Syntheses, structures and energetics of new enantiopure C₂-symmetric diols