메뉴 건너뛰기




Volumn 131, Issue 35, 2009, Pages 12570-12572

Mn(III)-mediated reactions of cyclopropanols with vinyl azides: Synthesis of pyridine and 2-azabicyclo[3.3.1]non-2-en-1-ol derivatives

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL GROUPS; CATALYTIC AMOUNTS; CHEMICAL EQUATIONS; CYCLOPROPANOL; DIVERGENT SYNTHESIS; IMINYL RADICALS; MEDIATED REACTIONS; ONE-ELECTRON OXIDATION; RADICAL ADDITION;

EID: 69849115537     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja905110c     Document Type: Article
Times cited : (271)

References (46)
  • 1
    • 84883545226 scopus 로고    scopus 로고
    • For recent reviews, see:(a) Gribble, G. W., Joule, J. A., Eds.; Elsevier: Oxford, and others in this series
    • For recent reviews, see:(a) Progress in Heterocyclic Chemistry; Gribble, G. W., Joule, J. A., Eds.; Elsevier: Oxford, 2008; Vol.20 and others in this series.
    • (2008) Progress in Heterocyclic Chemistry , vol.20
  • 2
    • 77955170036 scopus 로고    scopus 로고
    • Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Pergamon: Oxford
    • (b) Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Pergamon: Oxford, 2008.
    • (2008) Comprehensive Heterocyclic Chemistry III
  • 3
    • 0003607021 scopus 로고    scopus 로고
    • Katritzky, A. R., Rees, C. W., Scriven, E. F. V., McKillop, A., Eds.; Pergamon: Oxford, and references therein
    • (c) Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., McKillop, A., Eds.; Pergamon: Oxford, 1996 and references therein.
    • (1996) Comprehensive Heterocyclic Chemistry II
  • 6
    • 38749143594 scopus 로고    scopus 로고
    • For prior studies on iminyl radical formation from vinyl azides, see:(a)
    • For prior studies on iminyl radical formation from vinyl azides, see:(a) Montevecchi, P. C.; Navacchia, M. L.; Spagnolo, P. J. Org. Chem. 1997, 62, 5864.
    • (1997) J. Org. Chem. , vol.62 , pp. 5864
    • Montevecchi, P.C.1    Navacchia, M.L.2    Spagnolo, P.3
  • 8
    • 0001253023 scopus 로고    scopus 로고
    • For reviews of synthesis of aza-heterocycles using iminyl radicals, see:(a) Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim
    • For reviews of synthesis of aza-heterocycles using iminyl radicals, see:(a) Stella, L. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol.2, p 407.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 407
    • Stella, L.1
  • 12
    • 34547266358 scopus 로고    scopus 로고
    • For reports on the oxidative generation of β-carbonyl radicals from cyclopropanol derivatives and their addition to alkenes, see:(a)
    • For reports on the oxidative generation of β-carbonyl radicals from cyclopropanol derivatives and their addition to alkenes, see:(a) Hasewawa, E.; Yamaguchi, N.; Muraoka, H.; Tsuchida, H. Org. Lett. 2007, 9, 2811.
    • (2007) Org. Lett. , vol.9 , pp. 2811
    • Hasewawa, E.1    Yamaguchi, N.2    Muraoka, H.3    Tsuchida, H.4
  • 18
    • 35348959557 scopus 로고    scopus 로고
    • For recent reviews on synthesis of pyridines, see:(a)
    • For recent reviews on synthesis of pyridines, see:(a) Bagley, M. C.; Glover, C.; Merritt, E. A. Synlett 2007, 2459.
    • (2007) Synlett , pp. 2459
    • Bagley, M.C.1    Glover, C.2    Merritt, E.A.3
  • 23
    • 46949086690 scopus 로고    scopus 로고
    • For recent selected reports on synthesis of pyridines, see:(a)
    • For recent selected reports on synthesis of pyridines, see:(a) Manning, J. R.; Davies, H. M. L. J. Am. Chem. Soc. 2008, 130, 8602.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 8602
    • Manning, J.R.1    Davies, H.M.L.2
  • 35
    • 69849095019 scopus 로고    scopus 로고
    • note
    • For more details of screening of the reaction conditions, see Supporting Information.
  • 37
    • 69849109337 scopus 로고    scopus 로고
    • note
    • A proposed reaction mechanism on the formation of dihydropyrroles 4 was discussed in the Supporting Information.
  • 38
    • 69849111401 scopus 로고    scopus 로고
    • note
    • The structures of 4an, 6aa, 6ha, 6ab, 6ac, and 8 were determined by X-ray crystallographic analyses; see Supporting Information.
  • 46
    • 0031442284 scopus 로고    scopus 로고
    • For a report on C-C bond formation at bridgehead iminium cations to prepare 1-alkylated 2-azabicyclo[3.3.1]nonanes, see
    • For a report on C-C bond formation at bridgehead iminium cations to prepare 1-alkylated 2-azabicyclo[3.3.1]nonanes, see:Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280.
    • (1997) J. Org. Chem. , vol.62 , pp. 8280
    • Yamazaki, N.1    Suzuki, H.2    Kibayashi, C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.