I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
Chiral precursor of various reagents used in enantioselective syntheses./n
Forms a complex with lithium aluminum hydride, useful for the asymmetric reduction of ketones: J. Am. Chem. Soc., 101, 3129, 5843 (1979); alkynyl alcohols: Tetrahedron Lett., 22, 247 (1981); or steroidal enones: J. Chem. Soc., Chem. Commun., 115 (1981)./n
The complex with diisopropoxytitanium dichloride catalyzes the "glyoxylate ene reaction", in which glyoxylate ester adds to alkenes in a highly stereospecific manner: J. Am. Chem. Soc., 111, 1940 (1989):/n
For further example usingɑ-Methylstyrene, L03609, see: Org. Synth. Coll., 9, 596 (1998)./n
In combination with Titanium(IV) isopropoxide, A13703, catalyzes the asymmetric allylation of aldehydes using allylstannanes to give chiral homoallylic secondary alcohols: J. Am. Chem. Soc., 115, 8467 (1993). The same transformation has also been achieved using the dichlorotitanium complex: J. Am. Chem. Soc., 115, 7001 (1993)./n
Forms a chiral boron-containing Lewis acid which has been used in asymmetric Diels-Alder reactions: Tetrahedron, 49, 1749 (1993); J. Am. Chem. Soc., 115, 1151 (1993)./n
For diastereoselective alkyation of binaphthyl monoesters, see: J. Am. Chem. Soc., 117, 12159 (1995)./n
Used in combination with 2-Formylbenzeneboronic acid, B25434 in a protocol for determining the enantiomeric excess of primary amines by NMR: Org. Lett., 8, 609 (2006)./n
Reviews: BINOL: a C2-symmetric ligand for stereoselective C-C bond forming reactions: J. Prakt. Chem./ Chem. Ztg., 339, 758 (1997); Binaphthylic derivatives as chiral auxiliaries: Synthesis, 503 (1992); BINOL: a versatile chiral reagent: Chem. Rev., 105, 857 (2005)./n
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.