Synonym: (+)-2,2′-Dihydroxy-1,1′-dinaphthyl, (R)-(+)-1,1′-Binaphthalene-2,2′-diol, (R)-BINOL
|Related Categories||Asymmetric Synthesis, BINOLs, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes More...|
|optical activity||[α]21/D +34°, c = 1 in THF|
|optical purity||ee: 99% (HPLC)|
1, 5 g in glass bottle
10 g in poly bottle
A chiral auxiliary used in the catalytic asymmetric oxidation of sulfides to sulfoxides.1 Chiral lanthanide triflates formed from binaphthol serve as catalysts for asymmetric Diels-Alder reactions.2,3 Derivatives of binaphthol have recently found use in asymmetric Claisen rearrangements4 and asymmetric epoxidations.5 The lithium aluminum hydride derivative of these diols (BINAP-H) has been used extensively for the reduction of ketones.6
Chiral binapthol imminium salt precursor. Salts were used for an asymmetric epoxidation of olefins.
Certificate of Analysis
|Precautionary statements||P301 + P310-P305 + P351 + P338|
|Personal Protective Equipment||Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges|
|Hazard Codes (Europe)||T|
|Risk Statements (Europe)||25-36|
|Safety Statements (Europe)||26-45|
|RIDADR||UN 2811 6.1 / PGIII|
These chiral imine-ligands have recently been used in the vanadium-catalyzed oxidation of sulfides in conjunction with hydrogen peroxide. Optically active sulfoxides are obtained in high yields and e...
Aldrich ChemFiles 2005, 5.4, 7.
Keywords: Asymmetric synthesis, Catalysis, Ligands, Oxidations
1. J. Org. Chem. 58, 4529, (1993)
2. S. Kobayashi et al. Tetrahedron 50, 11623, (1994)
3. Hattori, K. Yamamoto, H. Synlett, 129, (1993)
4. Maruoka, K. et al. J. Am. Chem. Soc. 117, 1165, (1995)
5. Sasaki, H. et al. Synlett, 300, (1993)
6. Noyori, R. et al. J. Am. Chem. Soc. 106, 6709, 6717, (1984)
Fieser 12,190 / Fieser 15,135 / Fieser 16,132 / Fieser 17,116
Aldrich MSDS 1, 189:B / Corp MSDS 1 (1), 414:B / FT-IR 1 (1), 1111:A / FT-IR 2 (2), 1896:D / RegBook 1 (1), 1303:I / Sigma FT-IR 1 (2), 323:A / Structure Index 1, 199:C:2
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