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Volumn 128, Issue 8, 2006, Pages 2516-2517

Vinylcyclopropanation of olefins via 3-methoxy-1-propenylrhodium(I)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHOXY 1 PROPENYLRHODIUM; ALKENE; RHODIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33644660502     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0575326     Document Type: Article
Times cited : (55)

References (34)
  • 3
    • 0001373505 scopus 로고
    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford
    • (a) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1992; Vol. 5, p 899.
    • (1992) Comprehensive Organic Synthesis , vol.5 , pp. 899
    • Hudlicky, T.1    Reed, J.W.2
  • 9
    • 18044386806 scopus 로고    scopus 로고
    • and references therein
    • For those starting from enyne substrates, see: (e) Bruneau, C. Angew. Chem., Int. Ed. 2005, 44, 2328 and references therein.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 2328
    • Bruneau, C.1
  • 10
    • 0037419835 scopus 로고    scopus 로고
    • For relevant examples of rhodium-catalyzed multiple carbon-carbon bond-forming reactions, see: (a) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 1110
    • Cauble, D.F.1    Gipson, J.D.2    Krische, M.J.3
  • 19
    • 33644651829 scopus 로고    scopus 로고
    • note
    • Small amounts of 2-norbornanone (2%), 1,2-adduct (4%), and α-tetralone (2%) were obtained as byproducts. For their structures and the mechanisms for their formation, see Supporting Information.
  • 28
    • 30144440079 scopus 로고    scopus 로고
    • For a recent example of three-membered ring closure facilitated by oxygen coordination, see: Ndungu, J. M.; Larson, K. K.; Sarpong, R. Org. Lett. 2005, 7, 5845.
    • (2005) Org. Lett. , vol.7 , pp. 5845
    • Ndungu, J.M.1    Larson, K.K.2    Sarpong, R.3
  • 30
    • 0032512015 scopus 로고    scopus 로고
    • For the use of 2-(alkenyl)benzo[1,3,2]dioxaborole in 1,4-addition to α,β-unsaturated ketones. see: Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8479
    • Takaya, Y.1    Ogasawara, M.2    Hayashi, T.3
  • 31
    • 33644661788 scopus 로고    scopus 로고
    • note
    • A mixture of regioisomers (92:8) was used. For the preparation of 7, see Supporting Information.
  • 32
    • 23044489277 scopus 로고    scopus 로고
    • and references therein
    • For cyclopropanation of norbornene derivatives catalyzed by transition metals, see: Bigeault, J.; Giordano, L.; Buono, G. Angew. Chem., Int. Ed. 2005, 44, 4753 and references therein.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 4753
    • Bigeault, J.1    Giordano, L.2    Buono, G.3
  • 33
    • 0027050516 scopus 로고
    • The alternative conformer with the carbon-carbon double bond orienting to the norbornane methylene bridge would suffer from steric repulsion in between. For an analogous stereoselectivity, see: Grigg, R.; Sridharan, V. Tetrahedron Lett. 1992, 33, 7965.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 7965
    • Grigg, R.1    Sridharan, V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.