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Volumn 128, Issue 1, 2006, Pages 52-53

Preparation of alkenyl cyclopropanes through a ruthenium-catalyzed tandem enyne metathesis-cyclopropanation sequence

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKENYL GROUP; CYCLOPROPANE; RUTHENIUM;

EID: 30744456533     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055993l     Document Type: Article
Times cited : (90)

References (38)
  • 1
    • 10044265227 scopus 로고    scopus 로고
    • The terms tandem, domino, cascade, concurrent, and sequential catalysis are used interchangeably without bias for the mechanistic implications of their emerging definitions. For further discussion, see: (a) Tietze, L. F.; Rackelmann, N. Pure Appl. Chem. 2004, 76, 1967.
    • (2004) Pure Appl. Chem. , vol.76 , pp. 1967
    • Tietze, L.F.1    Rackelmann, N.2
  • 9
    • 0037451439 scopus 로고    scopus 로고
    • For recent reviews of nonmetathetic processes involving Grubbs' catalysts, see: (a) Alcaide, B.; Almendros, P. Chem.-Eur. J. 2003, 9, 1258.
    • (2003) Chem.-Eur. J. , vol.9 , pp. 1258
    • Alcaide, B.1    Almendros, P.2
  • 20
    • 22444436962 scopus 로고    scopus 로고
    • For recent reviews of cyclopropanation reaction with ruthenium, see: (a) Nishiyama, H. Top. Organomet. Chem. 2004, 11, 81.
    • (2004) Top. Organomet. Chem. , vol.11 , pp. 81
    • Nishiyama, H.1
  • 26
    • 30744465517 scopus 로고    scopus 로고
    • note
    • This is in contrast to the cyclopropanations catalyzed by alkylidene 2 that were observed by Diver and co-workers (ref 10a). In any event, while cyclopropanation products were not observed, fumarate and maleate diazo decomposition products were present.
  • 30
    • 30744466339 scopus 로고    scopus 로고
    • note
    • The fumarates and maleates were major byproducts in this reaction.
  • 33
    • 0024469029 scopus 로고
    • For an example of similar cyclopropanation regioselectivity, see; Sen, S. E.; Prestwich, G. D. J. Med. Chem. 1989, 32, 2152.
    • (1989) J. Med. Chem. , vol.32 , pp. 2152
    • Sen, S.E.1    Prestwich, G.D.2
  • 35
    • 6344226411 scopus 로고    scopus 로고
    • and references therein
    • 31P NMR studies on modified olefin metathesis catalysts, see: Schmidt, B. J. Org. Chem. 2004, 69, 7672 and references therein.
    • (2004) J. Org. Chem. , vol.69 , pp. 7672
    • Schmidt, B.1
  • 36
    • 0034660543 scopus 로고    scopus 로고
    • The loss of metathesis activity upon treatment with diazoester suggests that metathesis active enoic ruthenium complexes are not being generated. For examples of these complexes, see: (a) Ulman, M.; Belderrain, T. R.; Grubbs, R. H. Tetrahedron Lett. 2000, 41, 4689.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 4689
    • Ulman, M.1    Belderrain, T.R.2    Grubbs, R.H.3
  • 38
    • 0000415049 scopus 로고
    • The requirement of a 1,3-diene in a cyclopropanation has been observed previously and may provide insight into the mechanistic course of this reaction. For example, see: Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 8916.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8916
    • Harvey, D.F.1    Lund, K.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.