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Volumn 62, Issue 21, 1997, Pages 7497-7499

Application of the sharpless asymmetric dihydroxylation methodology to the enantioselective preparation of 2,3-dihydroxytetrahydro-2-naphthoic esters

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC DIHYDROXYLATION; DEOXYGENATIONS; ENANTIOPURE; ENANTIOSELECTIVE PREPARATION; GAINING ACCESS; METHYL ESTERS;

EID: 15444368063     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo970873k     Document Type: Article
Times cited : (6)

References (37)
  • 3
    • 0001387037 scopus 로고
    • Washington, D.C.
    • Mander, L. N. Chem. Rev. (Washington, D.C.) 1992, 92, 573.
    • (1992) Chem. Rev. , vol.92 , pp. 573
    • Mander, L.N.1
  • 5
    • 0000067960 scopus 로고
    • Catalytic Asymmetric Dihydroxylation
    • Ojima, I., Ed.; VCH: Weinheim, Germany
    • (b) Johnson, R. A.; Sharpless, K. B. Catalytic Asymmetric Dihydroxylation, In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, Germany, 1993; pp 227-272.
    • (1993) Catalytic Asymmetric Synthesis , pp. 227-272
    • Johnson, R.A.1    Sharpless, K.B.2
  • 12
    • 84892617472 scopus 로고    scopus 로고
    • note
    • 8e,9 A more efficient synthesis was achieved starting from 1,7-dimethoxynaphthalene, and the details are presented in the Supporting Information.
  • 20
    • 0010291446 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: and references therein
    • Mander, L. N. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: 1991; Vol 8, pp 489-522 and references therein.
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 489-522
    • Mander, L.N.1
  • 22
    • 84892583102 scopus 로고    scopus 로고
    • note
    • 5a-c to be the more stable of the two isomers, so given time, the equilibrium will favor the thermodynamically more stable product.
  • 23
    • 84892599179 scopus 로고    scopus 로고
    • Available from Aldrich Chemical Co.
    • Available from Aldrich Chemical Co.
  • 25
    • 84892600178 scopus 로고    scopus 로고
    • note
    • For comparative purposes, the racemate was obtained by carrying out the identical reaction, in the absence of ligand, to afford (±)-8 in 89% yield. This reaction was appreciably slower, taking 18 h at room temperature.
  • 26
    • 84892616126 scopus 로고    scopus 로고
    • note
    • 17a-c was employed; details are provided in the Supporting Information. When the Kakisawa procedure was followed to completion, the absolute configuration at C3 was determined to be S. As the dihydroxylation is stereospecific, this means that the absolute stereochemistry at C2 must be R. As expected, the absolute configuration matches that predicted by the Sharpless stereoselectivity rules.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.