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18531-94-7 - R-(+)-2,2'-Dihydroxy-1,1'-dinaphthyl, 98% - R-(-)-1,1'-Bi-2-naphthol - A17689 - Alfa Aesar

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

CAS Number
18531-94-7
Synonyms
R-(-)-1,1'-Bi-2-naphthol

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

MDL
MFCD00004068

Chemical Properties

Formula
C20H14O2
Formula Weight
286.33
Melting point
208-211°

Literature References

Chiral precursor of various reagents used in enantioselective syntheses.

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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).

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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):

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

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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).

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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).

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

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

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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).

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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).

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GHS Hazard and Precautionary Statements

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.

Other References

Merck
14,1226
Beilstein
3616837
Harmonized Tariff Code
2907.29
TSCA
No

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