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Volumn 128, Issue 21, 2006, Pages 7050-7054

Highly chemo-, regio-, and stereoselective [3+2]-cyclization of activated and deactivated allenes with alkenyl fischer carbene complexes: A straightforward access to alkylidenecyclopentanone derivatives

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; CHROMIUM; COMPLEXATION; DERIVATIVES; ISOMERIZATION; RHODIUM; STEREOCHEMISTRY;

EID: 33744783130     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0586788     Document Type: Article
Times cited : (56)

References (38)
  • 1
    • 0346265937 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York
    • For recent reviews on Fischer carbene complexes, see: (a) Wulff, W. D. Comprehensive Organometallic Chemislry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12.
    • (1995) Comprehensive Organometallic Chemislry II , vol.12
    • Wulff, W.D.1
  • 10
    • 17744400729 scopus 로고    scopus 로고
    • For recent applications of the Dötz reaction, see: (b) Minatti, A.; Dötz, K. H. J. Org. Chem. 2005, 70, 3745.
    • (2005) J. Org. Chem. , vol.70 , pp. 3745
    • Minatti, A.1    Dötz, K.H.2
  • 13
    • 4544320494 scopus 로고    scopus 로고
    • Krause, N., Hashmi, A. S. K., Eds.; Wiley: Weinheim
    • For recent reviews, see: (a) Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley: Weinheim. 2004.
    • (2004) Modern Allene Chemistry
  • 14
    • 22944485617 scopus 로고    scopus 로고
    • (b) Ma, S. Chem. Rev. 2005, 105, 2829.
    • (2005) Chem. Rev. , vol.105 , pp. 2829
    • Ma, S.1
  • 26
    • 0028000459 scopus 로고
    • For an isolated [3+2] heterocyclization involving an α-carbonyl rhodium-(II) carbene and methoxyallene, see: Pirrung, M. C.; Zhang, J.; Morehead, A. T., Jr. Tetrahedron Lett. 1994, 35, 6229.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 6229
    • Pirrung, M.C.1    Zhang, J.2    Morehead Jr., A.T.3
  • 27
  • 28
    • 33744781180 scopus 로고    scopus 로고
    • note
    • The chemo-, regio-, and stereochemistry of compounds 3, 4, and 5 were ascertained by NMR experiments.
  • 30
    • 33744830744 scopus 로고    scopus 로고
    • note
    • 6, also catalyze efficiently the reaction to give compounds 7.
  • 31
    • 33744828417 scopus 로고    scopus 로고
    • note
    • The chemo, regio-, and stereochemistry of compounds 7 were ascertained by NMR experiments. Moreover, an X-ray analysis was performed on compound 7a.
  • 35
    • 33744789054 scopus 로고    scopus 로고
    • note
    • 2 were unsuccessful.
  • 36
    • 0034829401 scopus 로고    scopus 로고
    • (a) This mechanistic proposal was proposed in the case of rhodium carbenes and neutral allenes; see ref 6. (b) The [4+2]-cycloaddition has been recognized by H. M. L. Davies as a valid mechanism in the [3+2]-cyclization of rhodium(II) carbenes and methoxyalkenes; see: Davies, H. M. L.; Xiang, B.; Kong, N.; Stafford, D. G. J. Am. Chem. Soc. 2001, 123, 7461.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7461
    • Davies, H.M.L.1    Xiang, B.2    Kong, N.3    Stafford, D.G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.