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Volumn 60, Issue 52, 2004, Pages 12239-12247

Efficient intramolecular Diels-Alder reactions of ester-tethered 1,7,9-decatrienoates catalyzed by bis-aluminated trifluoromethanesulfonamide

Author keywords

1,7,9 Decatrienoate; Bidentate Lewis acid; Bis aluminated trifluoromethanesulfonamide; Intramolecular Diels Alder reaction

Indexed keywords

ALUMINUM DERIVATIVE; ESTER DERIVATIVE; FLUOROMETHANE; SULFONAMIDE;

EID: 9644260643     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.10.012     Document Type: Article
Times cited : (26)

References (35)
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    • Chapter 4.1 W. Oppolzer B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford 315
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    • Oppolzer, W.1
  • 2
    • 0002251962 scopus 로고
    • D.P. Curran JAI Greenwich, CT
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    • Roush, W.R.1
  • 3
    • 0000048482 scopus 로고
    • B.M. Trost I. Fleming Pergamon Oxford
    • W.R. Roush B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 5 1991 Pergamon Oxford 513 550
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 513-550
    • Roush, W.R.1
  • 4
    • 0003009874 scopus 로고
    • W.G. Dauben Wiley New York
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    • Ciganek, E.1
  • 17
    • 85064255250 scopus 로고
    • M.E. Jung Synlett 4 1990 186 190
    • (1990) Synlett , vol.4 , pp. 186-190
    • Jung, M.E.1
  • 31
    • 0000355339 scopus 로고
    • Elucidation of mechanistic detail, for example, based on the structure of the substrate-Lewis acid complex form and based on the stereochemical outcome in the IMDA reaction of alkoxy-instead of silyloxy-substituted substrate is the future subject. Concerning the substituent effect of silyloxy group on the transition state of the IMDA reaction, it was reported that silyloxy group at C7 position in the 2,8,10-undecatrienal derivatives preferentially occupies pseudo-axial position. See: J.A. Marshall, B.G. Shearer, and S.L. Crooks J. Org. Chem. 52 1987 1236 1245
    • (1987) J. Org. Chem. , vol.52 , pp. 1236-1245
    • Marshall, J.A.1    Shearer, B.G.2    Crooks, S.L.3
  • 32
    • 0000465243 scopus 로고
    • It was reported that the stereoselectivity of the IMDA reaction of 1,6,8-nonatrienoate 5 under the thermal conditions is low to give a mixture of oxabicyclo[4.3.0]nonene derivatives 6, see: see: White, J.D., Nolen, E.G., Jr., Miller, C.H., J. Org. Chem. 1986, 51, 1150-1152.
    • (1986) J. Org. Chem. , vol.51 , pp. 1150-1152
    • White, J.D.1    Nolen Jr., E.G.2    Miller, C.H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.