메뉴 건너뛰기




Volumn 64, Issue 7, 1999, Pages 2264-2271

Enantioselective synthesis of binaphthol derivatives by oxidative coupling of naphthol derivatives catalyzed by chiral diamine-copper complexes

Author keywords

[No Author keywords available]

Indexed keywords

COPPER DERIVATIVE; DIAMINE DERIVATIVE; NAPHTHOL DERIVATIVE;

EID: 0033515595     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981808t     Document Type: Article
Times cited : (315)

References (52)
  • 5
    • 0002459025 scopus 로고
    • For recent methods for direct optical resolution of BINOL, see: (a) Kawashima, M.; Hirayama, A. Chem. Lett. 1990, 2299-2300.
    • (1990) Chem. Lett. , pp. 2299-2300
    • Kawashima, M.1    Hirayama, A.2
  • 8
    • 33845278920 scopus 로고
    • For enantioselective synthesis of binaphthyl skeletons by methods other than those of asymmetric oxidation, see: (d) Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153-8156.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 8153-8156
    • Hayashi, T.1    Hayashizaki, K.2    Kiyoi, T.3    Ito, Y.4
  • 10
    • 0000182508 scopus 로고
    • For asymmetric synthesis of binaphthols including second-order asymmetric transformation, see: (a) Feringa, B.; Wynberg, H. Bioorg. Chem. 1978, 7, 397-408.
    • (1978) Bioorg. Chem. , vol.7 , pp. 397-408
    • Feringa, B.1    Wynberg, H.2
  • 31
    • 33947476790 scopus 로고
    • (a) Hay, A. S. J. Org. Chem. 1962, 27, 3320-3321.
    • (1962) J. Org. Chem. , vol.27 , pp. 3320-3321
    • Hay, A.S.1
  • 33
    • 0344228728 scopus 로고    scopus 로고
    • Cu(OH)Cl·TMEDA dimer (di-μ-hydroxo-bis[(N,N,N',N'-tetramethylethylenediamine)copper(II)] chloride) is now commercially available (TCI, D2542)
    • Cu(OH)Cl·TMEDA dimer (di-μ-hydroxo-bis[(N,N,N',N'-tetramethylethylenediamine)copper(II)] chloride) is now commercially available (TCI, D2542).
  • 35
    • 0029783236 scopus 로고    scopus 로고
    • and references therein
    • Silica gel column chromatography (hexanes-EtOAc) of 2e furnished fractions that differ in enantiomeric excess. We employed hexanes-EtOAc as eluent for removing unreacted 1e and then dichloromethane for complete elution of 2e. Fractionation of nonracemic chiral compound on achiral phase: Nicoud, R.-M.; Jaubert, J.-N.; Rupprecht, I.; Kinkel, J. Chirality 1996, 8, 234-243 and references therein.
    • (1996) Chirality , vol.8 , pp. 234-243
    • Nicoud, R.-M.1    Jaubert, J.-N.2    Rupprecht, I.3    Kinkel, J.4
  • 39
    • 0345522372 scopus 로고    scopus 로고
    • 4b
    • 4b
  • 42
    • 0001227706 scopus 로고
    • Conversion of 2e into 2a via Curtius rearrangement has been reported, though the chemical yield of the decarboxylation step is low. See: Akimoto, H.; Yamada, S. Tetrahedron 1971, 27, 5999-6009.
    • (1971) Tetrahedron , vol.27 , pp. 5999-6009
    • Akimoto, H.1    Yamada, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.