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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
해저드 설명서 (EU): H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
주의 설명서: 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.