메뉴 건너뛰기




Volumn 8, Issue 5, 1997, Pages 779-800

Catalytic asymmetric synthesis of protected α-hydroxy aldehydes and related 1,2-difunctional chiral building blocks. An enantioselective synthesis of (-)-exo- and (-)-endo-brevicomin

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; BREVICOMIN;

EID: 0031054129     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00036-0     Document Type: Article
Times cited : (32)

References (66)
  • 8
    • 33748233248 scopus 로고    scopus 로고
    • Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem 1996, 108, 449; Angew. Chem., Int. Ed. Engl. 1996, 35, 451.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 451
  • 11
    • 0001600844 scopus 로고    scopus 로고
    • Steinhagen, H; Helmchen, G. Angew. Chem 1996, 108, 2489; Angew. Chem., Int. Ed. Engl. 1996, 35, 2337 and references cited herein.
    • (1996) Angew. Chem , vol.108 , pp. 2489
    • Steinhagen, H.1    Helmchen, G.2
  • 12
    • 0041998168 scopus 로고    scopus 로고
    • and references cited herein
    • Steinhagen, H; Helmchen, G. Angew. Chem 1996, 108, 2489; Angew. Chem., Int. Ed. Engl. 1996, 35, 2337 and references cited herein.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2337
  • 15
    • 33748233841 scopus 로고
    • (b) Brieden, W.; Ostwald, R.; Knochel, P. Angew. Chem 1993, 705, 629; Angew. Chem., Int. Ed. Engl. 1993, 32, 582.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 582
  • 29
    • 37049111060 scopus 로고
    • 1H-NMR analysis of the corresponding O-acetyl-mandelates using (S)-(+)-O-acetyl-mandelic acid. In each case, a calibration sample using (±)-O-acetyl-mandelic acid was prepared: Parker, D. J. Chem. Soc., Perkin Trans. 2 1983, 83.
    • (1983) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 83
    • Parker, D.1
  • 30
    • 0342982521 scopus 로고    scopus 로고
    • note
    • 1H-NMR).
  • 34
    • 0343417858 scopus 로고    scopus 로고
    • note
    • 13C-NMR).
  • 36
    • 0342982520 scopus 로고    scopus 로고
    • note
    • 2 and following the reaction sequence described above.
  • 37
    • 0005999049 scopus 로고    scopus 로고
    • For an enantioselective synthesis of 1,2 amino alcohols with a chiral auxiliary see: Enders, D.; Haertwig, A.; Raabe, G.; Runsink, J. Angew. Chem. 1996, 108, 2540; Angew. Chem., Int. Ed. Engl. 1996, 55, 2388 and references cited herein.
    • (1996) Angew. Chem. , vol.108 , pp. 2540
    • Enders, D.1    Haertwig, A.2    Raabe, G.3    Runsink, J.4
  • 38
    • 0012440322 scopus 로고    scopus 로고
    • and references cited herein
    • For an enantioselective synthesis of 1,2 amino alcohols with a chiral auxiliary see: Enders, D.; Haertwig, A.; Raabe, G.; Runsink, J. Angew. Chem. 1996, 108, 2540; Angew. Chem., Int. Ed. Engl. 1996, 55, 2388 and references cited herein.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.55 , pp. 2388
  • 39
    • 0343417857 scopus 로고    scopus 로고
    • For addition of organometallic compounds to α-hydroxy carbonyl compounds see: Devant, R. M.; Radunz, H.-E. in Houben-Weyl, Methods of Organic Chemistry, Vol. E 21 b, p. 1196; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. (Eds.); Thieme: Stuttgart, 1995.
    • Houben-weyl, Methods of Organic Chemistry , vol.E 21 B , pp. 1196
    • Devant, R.M.1    Radunz, H.-E.2
  • 40
    • 0342982518 scopus 로고
    • Thieme: Stuttgart
    • For addition of organometallic compounds to α-hydroxy carbonyl compounds see: Devant, R. M.; Radunz, H.-E. in Houben-Weyl, Methods of Organic Chemistry, Vol. E 21 b, p. 1196; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. (Eds.); Thieme: Stuttgart, 1995.
    • (1995)
    • Helmchen, G.1    Hoffmann, R.W.2    Mulzer, J.3    Schaumann, E.4
  • 41
    • 0000730188 scopus 로고
    • (a) Reetz, M. T. Angew. Chem. 1984, 96, 542; Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
    • (1984) Angew. Chem. , vol.96 , pp. 542
    • Reetz, M.T.1
  • 42
    • 0010771837 scopus 로고
    • (a) Reetz, M. T. Angew. Chem. 1984, 96, 542; Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
    • (1984) Angew. Chem., Int. Ed. Engl. , vol.23 , pp. 556
  • 45
    • 37049071496 scopus 로고
    • and ref. 8e. For other asymmetric catalyzed addition of diorganozincs to β-and γ-silyloxy aldehydes, see ref. 8c and 8f
    • For other asymmetric catalyzed addition of diorganozincs to α-silyloxy aldehydes see: (a) Soai, K.; Shimada, C.; Takeuchi, M.; Itabashi, M. J. Chem. Soc., Chem. Commun. 1994, 567 and ref. 8e. For other asymmetric catalyzed addition of diorganozincs to β-and γ-silyloxy aldehydes, see ref. 8c and 8f.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 567
    • Soai, K.1    Shimada, C.2    Takeuchi, M.3    Itabashi, M.4
  • 47
    • 0021775497 scopus 로고
    • Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem 1985, 97, 1; Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
    • (1985) Angew. Chem., Int. Ed. Engl. , vol.24 , pp. 1
  • 49
    • 33748983103 scopus 로고
    • Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem 1995, 707, 1159; Angew. Chem., Int. Ed. Engl. 1995, 34, 1059.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 1059
  • 50
    • 0003607449 scopus 로고
    • Syntheses up to 1979 and Syntheses from 1979-1989, Ed. ApSimon, J.; Wiley: New York
    • Review: Mori, K. in The Total Synthesis of Natural Products, Vol. 4 (Syntheses up to 1979) and Vol. 9 (Syntheses from 1979-1989), Ed. ApSimon, J.; Wiley: New York, 1989.
    • (1989) The Total Synthesis of Natural Products , vol.4-9
    • Mori, K.1
  • 51
  • 54
    • 0342548155 scopus 로고    scopus 로고
    • 13C-NMR
    • 13C-NMR.
  • 57
    • 0343853771 scopus 로고    scopus 로고
    • note
    • b: -79.4).
  • 58
    • 84862015315 scopus 로고
    • For other applications of functionalized diorganozincs in natural product synthesis see: (a) Stadtmüller, H.; Knochel, P. Synlett 1995, 463.
    • (1995) Synlett , pp. 463
    • Stadtmüller, H.1    Knochel, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.