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Volumn 63, Issue 26, 1998, Pages 9812-9827

Cycloaddition of heteroatom-substituted 2-azaallyl anions with alkenes. Synthesis of 1-pyrrolines and bridged azabicyclic compounds

Author keywords

[No Author keywords available]

Indexed keywords

1 METHOXY 7 AZABICYCLO[2.2.1]HEPTANE DERIVATIVE; 1 METHOXY 8 AZABICYCLO[3.2.1]OCTANE DERIVATIVE; 1 PYRROLINE DERIVATIVE; 2 AZAALLYL ANION DERIVATIVE; AZABICYCLIC DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032567426     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981457i     Document Type: Article
Times cited : (32)

References (72)
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  • 34
    • 0001012389 scopus 로고
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    • Wittig, G.; Hesse, A. In Organic Syntheses; Noland, W. E., Ed.; Wiley: New York, 1988; Collect. Vol. VI, pp 901-905.
    • (1988) Organic Syntheses , vol.6 , pp. 901-905
    • Wittig, G.1    Hesse, A.2
  • 42
    • 20644438732 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Michigan
    • Stevens, E. P. Ph.D. Thesis, University of Michigan, 1997.
    • (1997)
    • Stevens, E.P.1
  • 49
    • 84988129057 scopus 로고
    • In recent unpublished results by Michael A. Walters (ParkeDavis Pharmaceutical Research), semiempirical calculations (PM328a modified for lithium28') were performed on the cycloadditions of MeC(X)NCH2(-)Li(+) (X = OMe, SMe, or NMe2) with a-methylstyrene. An idealized reaction coordinate involving a concerted cycloaddition was used. The 4-phenylpyrroline was predicted in all three cases. We thank Dr. Walters for sharing his results with us. (a) Stewart, J. J. P. J. Comput. Chem. 1989,10,209-220.
    • (1989) J. Comput. Chem. , pp. 209-220
    • Stewart, J.J.P.1
  • 51
    • 33847523609 scopus 로고    scopus 로고
    • For recent ab initio calculations on the cycloaddition of 2-azaallyl anions with alkenes, see
    • For recent ab initio calculations on the cycloaddition of 2-azaallyl anions with alkenes, see:
  • 53
    • 0032522104 scopus 로고    scopus 로고
    • (b) Neumann, F.; Lambert, C.; Schleyer, P. v. R. J. Am. Chem. Soc. 1998,120, 3357-3370. Note that Schleyer concludes that the cycloaddition of the parent 2-azaallyl anion CH2=N-CH2()Li(+) with ethylene proceeds by a stepwise rather than concerted process. We plan to reevaluate our computational results in light of Schleyer's work.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 3357-3370
    • Neumann, F.1    Lambert, C.2
  • 54
    • 0031025225 scopus 로고    scopus 로고
    • and references therein
    • A variety of cyclic azomethine ylides, both stabilized and nonstabilized, have been generated and used in dipolar cycloaddition reactions to afford bridged azabicyclic compounds. For representative examples, see: (a) Kozikowski, A. P.; Araldi, G. L.; Ball, R. G. J. Org. Chem 1997,62,503-509 and references therein.
    • (1997) J. Org. Chem , vol.62 , pp. 503-509
    • Kozikowski, A.P.1    Araldi, G.L.2    Ball, R.G.3
  • 59
    • 0000723216 scopus 로고
    • Cordell, G. A., Ed.; Academic Press: New York
    • Lounasmaa, M.; Tamrainen, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 44, pp 1-114.
    • (1993) The Alkaloids , vol.44 , pp. 1-114
    • Lounasmaa, M.1    Tamrainen, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.