메뉴 건너뛰기




Volumn 71, Issue 9, 2006, Pages 3533-3539

Synthesis of N,N-bis(3-butenyl)amines from 2-azaallyl dication synthetic equivalents and conversion to 2,3,6,7-tetrahydroazepines by ring-closing metathesis

Author keywords

[No Author keywords available]

Indexed keywords

MONOALLYLATION; RING-CLOSING METATHESIS; TETRAHYDROAZEPINES;

EID: 33646256843     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060173s     Document Type: Article
Times cited : (17)

References (64)
  • 1
    • 0000716787 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK
    • Selected reviews: (a) Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 1, pp 355-396.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 355-396
    • Volkmann, R.A.1
  • 2
    • 0000018912 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK
    • (b) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 2, pp 975-1006.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 975-1006
    • Kleinman, E.F.1    Volkmann, R.A.2
  • 4
  • 24
    • 33646267393 scopus 로고    scopus 로고
    • note
    • 9a
  • 27
    • 0008051816 scopus 로고
    • For methods of preparation of the modified Strecker adducts see: (a) Paventi, M.; Edward, J. T. Can. J. Chem. 1987, 65, 282.
    • (1987) Can. J. Chem. , vol.65 , pp. 282
    • Paventi, M.1    Edward, J.T.2
  • 34
    • 0036251136 scopus 로고    scopus 로고
    • For a recent review of diastereoselectivity in addition to imines bearing stereogenic N-substituents, see: (a) Alvaro, G.; Savoia, D. Synlett 2002, 651.
    • (2002) Synlett , pp. 651
    • Alvaro, G.1    Savoia, D.2
  • 39
    • 0003529785 scopus 로고    scopus 로고
    • Silverman, G. S., Rakita, P. E., Eds.; Marcel Dekker: New York
    • (a) Handbook of Grignard Reagents; Silverman, G. S., Rakita, P. E., Eds.; Marcel Dekker: New York, 1996.
    • (1996) Handbook of Grignard Reagents
  • 40
    • 1442360812 scopus 로고    scopus 로고
    • and references therein
    • (b) Hoffmann, R. W. Chem. Soc. Rev. 2003, 32, 225 and references therein.
    • (2003) Chem. Soc. Rev. , vol.32 , pp. 225
    • Hoffmann, R.W.1
  • 44
    • 0003464699 scopus 로고    scopus 로고
    • Fürstner, A., Ed.; Springer-Verlag: Heidelberg, Germany
    • (d) Alkene Metathesis in Organic Synthesis; Fürstner, A., Ed.; Springer-Verlag: Heidelberg, Germany, 1998.
    • (1998) Alkene Metathesis in Organic Synthesis
  • 49
    • 0001811974 scopus 로고    scopus 로고
    • Recent reviews focusing on ring-closing metathesis of nitrogen-containing compounds: (a) Phillips, A. J.; Abell, A. D. Aldrichim. Acta 1999, 32, 75.
    • (1999) Aldrichim. Acta , vol.32 , pp. 75
    • Phillips, A.J.1    Abell, A.D.2
  • 51
    • 0033930445 scopus 로고    scopus 로고
    • Dixneuf and co-workers have reported related methodology, where N-Cbz imines were combined with allylmagnesium bromide or 3-butenyl-magnesium bromide followed by N-allylation to afford 4-aza-l,7-octadienes or 4-aza-1,8-nonadienes, respectively, which were subjected to RCM to afford 1,2,5,6- tetrahydropiperidines or 2,5,6,7-tetrahydroazepines, isomers of the tetrahydroazepines reported herein. See: (a) Osipov, S. N.; Artyushin, O. I.; Kolomiets, A. F.; Bruneau, C.; Dixneuf, P. H. Synlett 2000, 1031.
    • (2000) Synlett , pp. 1031
    • Osipov, S.N.1    Artyushin, O.I.2    Kolomiets, A.F.3    Bruneau, C.4    Dixneuf, P.H.5
  • 56
    • 0033536462 scopus 로고    scopus 로고
    • For RCMs of N,N-bis(3-butenyl)amine derivatives to 2,3,6,7- tetrahydroazepines, see the following: (f) Paquette, L. A.; Leit, S. M. J. Am. Chem. Soc. 1999, 121, 8126.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 8126
    • Paquette, L.A.1    Leit, S.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.