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Volumn 73, Issue 11, 2008, Pages 4237-4240

Chemoselective functionalization of 3,3′-substituted BINOL derivatives

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; PHENOLS;

EID: 44949089644     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800315s     Document Type: Article
Times cited : (24)

References (42)
  • 1
    • 0000718373 scopus 로고    scopus 로고
    • (a) Pu, L. Chem. Rev. 1998, 98, 2405-2494.
    • (1998) Chem. Rev , vol.98 , pp. 2405-2494
    • Pu, L.1
  • 2
    • 17244369977 scopus 로고    scopus 로고
    • (b) Brunel, J. M. Chem. Rev. 2005, 105, 857-898.
    • (2005) Chem. Rev , vol.105 , pp. 857-898
    • Brunel, J.M.1
  • 26
    • 44949159239 scopus 로고    scopus 로고
    • Athough 3,3′-formylation of MOM-protected BINOL has also been reported by these authors, its purification was more problematic than in the case of compound (R)-2. Deprotection protocols for MOM protecting groups, however, usually require harsh acidic conditions that can be unsuitable for acid-sensitive substrates such as benzoyl or benzyl esters.
    • (b) Athough 3,3′-formylation of MOM-protected BINOL has also been reported by these authors, its purification was more problematic than in the case of compound (R)-2. Deprotection protocols for MOM protecting groups, however, usually require harsh acidic conditions that can be unsuitable for acid-sensitive substrates such as benzoyl or benzyl esters.
  • 27
    • 0019420966 scopus 로고
    • 3 cleaves both OMe protecting groups and acetate esters on polyphenolyic aromatic substrates. See, for example
    • 3 cleaves both OMe protecting groups and acetate esters on polyphenolyic aromatic substrates.
    • (1981) Tetrahedron Lett , vol.22 , pp. 899-902
    • Nagaoka, N.1    Schmid, G.2    Iio, H.3    Kishi, Y.4
  • 31
    • 0036642529 scopus 로고    scopus 로고
    • For base activation of quinone - methides, see: (a) Van De Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367-5405. See also:
    • For base activation of quinone - methides, see: (a) Van De Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367-5405. See also:
  • 33
    • 44949184034 scopus 로고    scopus 로고
    • In control experiments run under the same mildly basic conditions, alkylation of BINOL (R)-1 proceeds quantitatively. Alkylation of dialdehyde (R)-4, instead, gives decomposition products.
    • In control experiments run under the same mildly basic conditions, alkylation of BINOL (R)-1 proceeds quantitatively. Alkylation of dialdehyde (R)-4, instead, gives decomposition products.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.