A17689 R-(+)-2,2'-Dihydroxy-1,1'-dinaphthyl, 98%

R-(+)-2,2'-Dihydroxy-1,1'-dinaphthyl, 98%

Chemische Eigenschaften

Literaturverweise

Chiral precursor of various reagents used in enantioselective syntheses.

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).

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):

For further example usingɑ-Methyl­styrene, L03609, see: Org. Synth. Coll., 9, 596 (1998).

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).

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).

See also (R)-(+)-2,2'-Bis(diphenyl­phosphino)-1,1'-binaphthyl­, B23785.

For diastereoselective alkyation of binaphthyl monoesters, see: J. Am. Chem. Soc., 117, 12159 (1995).

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).

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).