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Volumn 3, Issue 7, 2001, Pages 1049-1052

An enantioselective synthesis of benzylidene-protected syn-3,5-dihydroxy carboxylate esters via osmium, palladium, and base catalysis

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ARTICLE;

EID: 0000417893     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0156188     Document Type: Article
Times cited : (68)

References (45)
  • 4
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    • note
    • Leighton has demonstrated that this can be accomplished with allyl-(-)-diisopinocamphenylborane and (E)-crotyl-(-)-diisopinocamphenylborane.
  • 12
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    • For good reviews see: (a) Hoffmann, R. W. Pure Appl. Chem. 1988, 60(1), 123-30.
    • (1988) Pure Appl. Chem. , vol.60 , Issue.1 , pp. 123-130
    • Hoffmann, R.W.1
  • 29
    • 0042790515 scopus 로고
    • For vinylogous aldol approaches to δ-hydroxy-1-enoates, see: (a) Fleming, I. Bull. Soc. Chem. Fr. 1981, 2, 7-13.
    • (1981) Bull. Soc. Chem. Fr. , vol.2 , pp. 7-13
    • Fleming, I.1
  • 34
    • 0000016656 scopus 로고
    • Previously Sharpless had shown that the AD mix reagent dihydroxylates simple dienoates 6a and 6c with good enantio-and diastereo-control, see: (a) Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570-7571.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7570-7571
    • Xu, D.1    Crispino, G.A.2    Sharpless, K.B.3
  • 36
    • 33947086629 scopus 로고
    • All levels of enantioinduction were determined by HPLC analysis (8% IPA/Hexane, Chiralcel OD) and/or Mosher ester analysis. (a) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143.
    • (1973) J. Org. Chem. , vol.38 , pp. 2143
    • Sullivan, G.R.1    Dale, J.A.2    Mosher, H.S.3
  • 38
    • 0042289408 scopus 로고    scopus 로고
    • note
    • 13C NMR, FTIR, HRMS, and/or elemental analysis.
  • 41
    • 0041788330 scopus 로고    scopus 로고
    • note
    • Furthermore, the ratios of 9/6a and 10/6a for both reactions were equivalent at both low and high conversion.
  • 42
    • 0042289409 scopus 로고    scopus 로고
    • note
    • These results do not preclude the mechanistic possibility for the formation of ethyl sorbate via a β,γ-unsaturated regioisomer of 9 and 10 and subsequent base-and/or palladium-catalyzed elimination.
  • 43
    • 0001224655 scopus 로고
    • We found the Rychnovsky phenol variant of the Trost procedure was the best for these substrates. (a) Rychnovsky, S. D.; Kim, J. J. Org. Chem. 1994, 59, 2659-60. For the original Trost procedure, see:
    • (1994) J. Org. Chem. , vol.59 , pp. 2659-2660
    • Rychnovsky, S.D.1    Kim, J.2
  • 45
    • 0042289407 scopus 로고    scopus 로고
    • note
    • Benzaldehyde (1.1 equiv) with 0.1 equiv of KOt-Bu; after 15 min more benzaldehyde (1.1 equiv) and KOt-Bu (0.1 equiv).


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