Nucleophilic substitution of aromatic fluorine in F(8)BINOL offers the possibility of selectively introducing a variety of substituents at the 6, 6', 7, and 7' positions. The configurational integrity of the homochiral precursors is maintained under the conditions described, allowing one to carry out these modification protocols on a microscale without the need for subsequent resolution steps. The resulting chiral ligands have been investigated as precursors to new asymmetric catalysts.
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Regioselective substitution of fluorine in F(8)BINOL as a versatile route to new ligands with axial chirality.
Org Lett
November 2000
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6 Canada.
Nucleophilic substitution of aromatic fluorine in F(8)BINOL offers the possibility of selectively introducing a variety of substituents at the 6, 6', 7, and 7' positions. The configurational integrity of the homochiral precursors is maintained under the conditions described, allowing one to carry out these modification protocols on a microscale without the need for subsequent resolution steps. The resulting chiral ligands have been investigated as precursors to new asymmetric catalysts.
View Article and Find Full Text PDFF8BINOL, an electronically perturbed version of BINOL with remarkable configurational stability.
Org Lett
January 2000
Department of Chemistry, University of Toronto, Ontario, Canada.
[structure: see text] Substitution of hydrogens by fluorines at the 5, 5', 6, 6', 7, 7', 8, and 8' positions of BINOL strongly affects distribution of electron density within the biaryl skeleton but has a very small influence on the torsion angle. The most important consequence of this structural alteration is the dramatic increase in configurational stability of homochiral F8BINOL.
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