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Volumn 126, Issue 42, 2004, Pages 13708-13713

Application of chiral cationic catalysts to several classical syntheses of racemic natural products transforms them into highly enantioselective pathways

Author keywords

[No Author keywords available]

Indexed keywords

POSITIVE IONS; SEPARATION; SYNTHESIS (CHEMICAL); VITAMINS;

EID: 6444234868     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046154m     Document Type: Article
Times cited : (109)

References (38)
  • 15
    • 0004208435 scopus 로고
    • Reinhold Publishing Co.: New York
    • See also (a) Fieser, L. F.; Fieser, M. Steroids; Reinhold Publishing Co.: New York, 1959; pp 711-713. (b) Blickenstaff, R. T.; Gosh, A. C.; Wolf, G. C. Total Synthesis of Steroids; Academic Press: New York, 1974; pp 182-187.
    • (1959) Steroids , pp. 711-713
    • Fieser, L.F.1    Fieser, M.2
  • 16
    • 0003713229 scopus 로고
    • Academic Press: New York
    • See also (a) Fieser, L. F.; Fieser, M. Steroids; Reinhold Publishing Co.: New York, 1959; pp 711-713. (b) Blickenstaff, R. T.; Gosh, A. C.; Wolf, G. C. Total Synthesis of Steroids; Academic Press: New York, 1974; pp 182-187.
    • (1974) Total Synthesis of Steroids , pp. 182-187
    • Blickenstaff, R.T.1    Gosh, A.C.2    Wolf, G.C.3
  • 17
    • 6444230761 scopus 로고    scopus 로고
    • note
    • On a larger scale the use of 5 mol % catalyst 8 would probably suffice since the reaction could be run at higher concentrations of the Diels-Alder components. In any event (S)-diphenylprolinol, from which catalyst 8 is derived, is readily recovered for reuse.
  • 18
    • 6444227812 scopus 로고    scopus 로고
    • note
    • Enantiomeric purity was determined by gas chromatographic analysis on a chiral γ-TA column.
  • 21
    • 6444227810 scopus 로고    scopus 로고
    • note
    • The enantiomer of catalyst 26 obviously could be used for the enantioselective synthesis of 25.
  • 26
    • 0036263839 scopus 로고    scopus 로고
    • For a recent review of such enantioselective Diels-Alder routes see Corey, E. I. Angew. Chem., Int. Ed. 2002, 41, 1650-1667.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1650-1667
    • Corey, E.I.1
  • 30
    • 6444222577 scopus 로고    scopus 로고
    • note
    • The absolute configuration of adduct 35 follows from analogy with a large number of related examples (see ref 1).
  • 33
    • 0000494450 scopus 로고    scopus 로고
    • For the synthesis of the chiral α,β-enone 38, see Sarakinos, G.; Corey, E. J. Org. Lett. 1999, 1, 811-814.
    • (1999) Org. Lett. , vol.1 , pp. 811-814
    • Sarakinos, G.1    Corey, E.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.