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Volumn 3, Issue 9, 2001, Pages 1327-1330

Double allylation reactions of (2-azaallyl)stannanes: Synthesis of N,N-bis(3-butenyl)amines and their conversion to 2,3,6,7-tetrahydroazepines via ring-closing metathesis

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINE; AZEPINE DERIVATIVE; TIN DERIVATIVE;

EID: 0035799875     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015711w     Document Type: Article
Times cited : (19)

References (37)
  • 1
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    • See the following recent papers and the earlier work cited therein: (a) Pearson, W. H.; Lovering, F. E. J. Org. Chem. 1998, 63, 3607-3617.
    • (1998) J. Org. Chem. , vol.63 , pp. 3607-3617
    • Pearson, W.H.1    Lovering, F.E.2
  • 5
    • 0000716787 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • Selected reviews: (a) Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 355-396.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 355-396
    • Volkmann, R.A.1
  • 6
    • 0000018912 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press; Oxford
    • (b) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press; Oxford, 1991; Vol. 2, pp 975-1006.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 975-1006
    • Kleinman, E.F.1    Volkmann, R.A.2
  • 8
    • 0038106171 scopus 로고    scopus 로고
    • (d) Bloch, R. Chem. Rev. 1998, 98, 8, 1407-1438.
    • (1998) Chem. Rev. , vol.98 , Issue.8 , pp. 1407-1438
    • Bloch, R.1
  • 11
    • 0034729582 scopus 로고    scopus 로고
    • Wright and co-workers have reported related methodology, where N-allyl imines were combined with allylmagnesium bromide to afford 4-aza-1,7-octadienes, which were subjected to ring-closing metathesis to afford 1,2,5,6-tetrahydropyridines. Difficulty adding other organometallics was encountered. See: Wright, D. L.; Schulte, J. P.; Page, M. A. Org. Lett. 2000, 2, 1847-1850.
    • (2000) Org. Lett. , vol.2 , pp. 1847-1850
    • Wright, D.L.1    Schulte, J.P.2    Page, M.A.3
  • 12
    • 0002446724 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford
    • Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2. p 1.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1
    • Roush, W.R.1
  • 16
    • 0042120472 scopus 로고    scopus 로고
    • note
    • 9 but not isolated prior to the current work.
  • 17
    • 0042621614 scopus 로고    scopus 로고
    • note
    • 3, 100 MHz) δ 155.22, 151.59, 151.47, 135.94, 135.57, 135.41, 129.56, 129.20, 125.11, 125.02, 121.75, 121.70, 117.15, 116.78, 116.55, 116.41, 64.48 (br), 45.02 (br), 35.31, 34.95, 34.34, 32.98, 31.49, 31.00, 20.49, 20.41, 20.34.
  • 25
    • 0001811974 scopus 로고    scopus 로고
    • For a review focusing on ring-closing metathesis of nitrogen-containing compounds, see: (a) Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75-89. For recent references in this general area, see:
    • (1999) Aldrichimica Acta , vol.32 , pp. 75-89
    • Phillips, A.J.1    Abell, A.D.2
  • 31
    • 0033930445 scopus 로고    scopus 로고
    • Osipov and co-workers have reported related methodology, where N-Cbz imines were combined with allylmagnesium bromide or 3-butenylmagnesium bromide followed by N-allylation to afford 4-aza-1,7-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, 1031-1033. For other imine allylation/RCM work, see:
    • (2000) Synlett , pp. 1031-1033
    • Osipov, S.N.1    Artyushin, O.I.2    Kolomiets, A.F.3    Bruneau, C.4    Dixneuf, P.H.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.