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Volumn 9, Issue 4, 2007, Pages 703-706

Intramolecular azide trapping of the Nazarov intermediate: Formation of peroxy-bridged indolizidinones via a deep-seated rearrangement and aerobic oxidation

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; BETAINE; BRIDGED COMPOUND; INDOLIZINE DERIVATIVE;

EID: 33847775609     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070053m     Document Type: Article
Times cited : (52)

References (32)
  • 1
    • 7044235263 scopus 로고    scopus 로고
    • (a) Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
    • (1996) Chem. Rev , vol.96 , pp. 115-136
    • Tietze, L.F.1
  • 6
    • 22544443923 scopus 로고    scopus 로고
    • Recent examples: (a) White, T. D.; West, F. G. Tetrahedron Lett. 2005, 46, 5629-5632.
    • Recent examples: (a) White, T. D.; West, F. G. Tetrahedron Lett. 2005, 46, 5629-5632.
  • 13
    • 24044531286 scopus 로고    scopus 로고
    • For recent reviews concerning the reaction of azides with electrophiles, see: a
    • For recent reviews concerning the reaction of azides with electrophiles, see: (a) Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188-5240.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 5188-5240
    • Bräse, S.1    Gil, C.2    Knepper, K.3    Zimmermann, V.4
  • 15
    • 85065824229 scopus 로고
    • For other examples of formation of transient 1,4-dipoles and their subsequent 1,5-hydrogen shifts, see: a
    • For other examples of formation of transient 1,4-dipoles and their subsequent 1,5-hydrogen shifts, see: (a) Lenz, G. R. Synthesis 1978, 489-518.
    • (1978) Synthesis , pp. 489-518
    • Lenz, G.R.1
  • 23
    • 33847787537 scopus 로고    scopus 로고
    • See Supporting Information for a discussion of the relative configuration of the major isomer of 12a
    • See Supporting Information for a discussion of the relative configuration of the major isomer of 12a.
  • 24
    • 0141855021 scopus 로고    scopus 로고
    • We have previously observed that dienones incorporating a cyclopentene ring undergo electrocyclization at a much slower rate, presumably due to ring strain in the resulting bicyclo[3.3.0]octenyl cation: Wang, Y.; Schul, B. D.; Arif, A. M.; West, F. G. Org. Lett. 2003, 5, 2747-2750.
    • We have previously observed that dienones incorporating a cyclopentene ring undergo electrocyclization at a much slower rate, presumably due to ring strain in the resulting bicyclo[3.3.0]octenyl cation: Wang, Y.; Schul, B. D.; Arif, A. M.; West, F. G. Org. Lett. 2003, 5, 2747-2750.
  • 26
    • 33847781535 scopus 로고    scopus 로고
    • In preliminary studies, we have found that monocyclic betaines analogous to 3 undergo a rapid 1,5-hydrogen shift with no detectable peroxide formation: Song, D.; Rostami, A.; West, F. G. unpublished results.
    • In preliminary studies, we have found that monocyclic betaines analogous to 3 undergo a rapid 1,5-hydrogen shift with no detectable peroxide formation: Song, D.; Rostami, A.; West, F. G. unpublished results.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.