F8BINOL, an Electronically Perturbed Version of BINOL with Remarkable Configurational Stability
- 18 December 1999
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (1) , 41-44
- https://doi.org/10.1021/ol991244v
Abstract
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.Keywords
This publication has 14 references indexed in Scilit:
- Enantioselective conjugate addition of diethylzinc to cyclic enones catalyzed by chiral copper complexes containing a new phosphorus ligand with an H8-binaphthoxy moietyTetrahedron: Asymmetry, 1998
- The Mechanistic Basis for Electronic Effects on Enantioselectivity in the (salen)Mn(III)-Catalyzed Epoxidation ReactionJournal of the American Chemical Society, 1998
- 3,3′-dinitro-octahydrobinaphthol: A new chiral ligand for metal-catalyzed enantioselective reactionsTetrahedron Letters, 1997
- Novel Asymmetric Alkylation of Aromatic Aldehydes with Triethylaluminum Catalyzed by Titanium·(1,1‘-bi-2-naphthol) and Titanium·(5,5‘,6,6‘,7,7‘,8,8‘-octahydro-1,1‘- bi-2-naphthol) ComplexesJournal of the American Chemical Society, 1997
- Formation of racemic compound crystals by mixing of two enantiomeric crystals in the solid state. Liquid transport of molecules from crystal to crystalJournal of the Chemical Society, Perkin Transactions 2, 1997
- A Widely Applicable Method of Resolution of Binaphthyls: Preparation of Enantiomerically Pure 1,1'- Binaphthalene-2,2'-diol, 1,1'-Binaphthalene-2,2'-dithiol, 2'-Mercapto-1,1'-binaphthalen-2-ol, and 1,1'-Binaphthalene-8,8'-diolThe Journal of Organic Chemistry, 1995
- Diastereoselective and enantioselective glyoxylate-ene reaction catalyzed by new class of binaphthol-derived titanium complexTetrahedron Letters, 1994
- Efficient synthesis of (R)- and (S)-(6,6′-difluorobiphenyl-2,2′-diyl) bis(diphenylphosphine); electron-poor biphenyl-type ligands for transition metal catalysts.Tetrahedron: Asymmetry, 1994
- Asymmetric hetero-Diels-Alder reaction catalyzed by a chiral organoaluminum reagentJournal of the American Chemical Society, 1988
- Host-guest complexation. 7. The binaphthyl structural unit in host compoundsThe Journal of Organic Chemistry, 1977