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Volumn 53, Issue 37, 2014, Pages 9904-9908

Expedient synthesis of fused azepine derivatives using a sequential rhodium(II)-catalyzed cyclopropanation/1-aza-Cope rearrangement of dienyltriazoles

Author keywords

azavinylcarbene; dihydroazepine; heterocycles; rearrangements; rhodium

Indexed keywords

CHEMICAL REACTIONS; CHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 84906948859     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201405356     Document Type: Article
Times cited : (132)

References (52)
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    • For a similar methodology using alkynes instead of allenes, see
    • For a similar methodology using alkynes instead of allenes, see:, Y. Shi, V. Gevorgyan, Org. Lett. 2013, 15, 5394-5396
    • (2013) Org. Lett. , vol.15 , pp. 5394-5396
    • Shi, Y.1    Gevorgyan, V.2
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    • 79960178492 scopus 로고    scopus 로고
    • For an intermolecular version of this reaction, see
    • For an intermolecular version of this reaction, see:, B. Chattopadhyay, V. Gevorgyan, Org. Lett. 2011, 13, 3746-3749
    • (2011) Org. Lett. , vol.13 , pp. 3746-3749
    • Chattopadhyay, B.1    Gevorgyan, V.2
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    • 84901617584 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2014, 53, 5662-5666.
    • (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 5662-5666
  • 45
    • 84906949680 scopus 로고    scopus 로고
    • Such a 1,2-hydride shift has been shown to be a significant side-reaction for other α-alkyl azavinyl-substituted rhodium carbenoids. For example, see Refs. [8c and 8e].
    • Such a 1,2-hydride shift has been shown to be a significant side-reaction for other α-alkyl azavinyl-substituted rhodium carbenoids. For example, see Refs. [8c and 8e].
  • 46
    • 84906949672 scopus 로고    scopus 로고
    • metal carbenoid substituents have been hypothesized to favor cyclopropanation over 1,2-hydride migration for intermolecular reactions
    • II and the metal carbenoid substituents have been hypothesized to favor cyclopropanation over 1,2-hydride migration for intermolecular reactions
    • II
  • 50
    • 84906949673 scopus 로고    scopus 로고
    • CCDC 998199 (2 a) and CCDC 998200 (4) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
  • 51
    • 84886913357 scopus 로고    scopus 로고
    • Similar substitution effects have recently been demonstrated to significantly slow down the divinylcyclopropane rearrangement with various derivatives, by impeding the adoption of the requisite boat conformation needed for the [3,3] sigmatropic rearrangement to take place.
    • Similar substitution effects have recently been demonstrated to significantly slow down the divinylcyclopropane rearrangement with various derivatives, by impeding the adoption of the requisite boat conformation needed for the [3,3] sigmatropic rearrangement to take place., J. D. Osler, W. P. Unsworth, R. J. K. Taylor, Org. Biomol. Chem. 2013, 11, 7587.
    • (2013) Org. Biomol. Chem. , vol.11 , pp. 7587
    • Osler, J.D.1    Unsworth, W.P.2    Taylor, R.J.K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.