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Volumn 9, Issue 16, 2007, Pages 3081-3084

Medium-sized carbocycles by a zirconocene-catalyzed tandem formal ring Expansion - Magnesation reaction of alkenyl-substituted cyclic enol ethers

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ETHER DERIVATIVE; MAGNESIUM; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG; ZIRCONIUM; ZIRCONOCENE DICHLORIDE;

EID: 34547944433     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071137y     Document Type: Article
Times cited : (6)

References (38)
  • 8
    • 0026721571 scopus 로고
    • For some leading reviews, see: a
    • For some leading reviews, see: (a) Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757-5821.
    • (1992) Tetrahedron , vol.48 , pp. 5757-5821
    • Petasis, N.A.1    Patane, M.A.2
  • 12
    • 0034246704 scopus 로고    scopus 로고
    • (e) Yet, L. Chem. Rev. 2000, 100, 2963-3008.
    • (2000) Chem. Rev , vol.100 , pp. 2963-3008
    • Yet, L.1
  • 17
    • 34547950047 scopus 로고    scopus 로고
    • In this context, the impressive work developed by I. Marek and co-workers should be noted (see: Chinkov, N.; Marek, I. In New Aspects of Zirconium Containing Organic Compounds, Topics In Organomet. Chem.; Marek, I., Ed.; Springer: Berlin, 2005; 10).
    • In this context, the impressive work developed by I. Marek and co-workers should be noted (see: Chinkov, N.; Marek, I. In New Aspects of Zirconium Containing Organic Compounds, Topics In Organomet. Chem.; Marek, I., Ed.; Springer: Berlin, 2005; Vol. 10).
  • 19
    • 23744461967 scopus 로고    scopus 로고
    • Also, for a recent interesting cyclization reaction of enol ether derivatives mediated by zirconium complexes, see
    • Also, for a recent interesting cyclization reaction of enol ether derivatives mediated by zirconium complexes, see: Owen, D. R.; Whitby, R. J. Synthesis 2005, 2061-2074.
    • (2005) Synthesis , pp. 2061-2074
    • Owen, D.R.1    Whitby, R.J.2
  • 20
    • 4544225883 scopus 로고    scopus 로고
    • For some recent papers, see: a
    • For some recent papers, see: (a) Tan, Z.; Negishi, E. Angew. Chem., Int. Ed. 2004, 43, 2911-2914.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 2911-2914
    • Tan, Z.1    Negishi, E.2
  • 30
    • 34547943587 scopus 로고    scopus 로고
    • The structures and relative configuration were unequivocally determined by NMR experiments COSY, HMQC, HMBC, and NOESY
    • The structures and relative configuration were unequivocally determined by NMR experiments (COSY, HMQC, HMBC, and NOESY).
  • 31
    • 34547938428 scopus 로고    scopus 로고
    • It should be noted that the outcome of the intramolecular reaction of an alkene-zirconocene complex and a six-membered cyclic enol ether is different from the intermolecular version of the reaction; see ref 3b
    • It should be noted that the outcome of the intramolecular reaction of an alkene-zirconocene complex and a six-membered cyclic enol ether is different from the intermolecular version of the reaction; see ref 3b.
  • 32
    • 34547926577 scopus 로고    scopus 로고
    • Although a Zr-alkoxide elimination reaction could be proposed on intermediate 3, this option would afford a constrained bicyclic oxazirconocene complex. For this reason, an initial Mg, Zr exchange is proposed as the most likely step. Support for this mechanism may be found in the work developed by Hoveyda et al. See ref 5g
    • Although a Zr-alkoxide elimination reaction could be proposed on intermediate 3, this option would afford a constrained bicyclic oxazirconocene complex. For this reason, an initial Mg - Zr exchange is proposed as the most likely step. Support for this mechanism may be found in the work developed by Hoveyda et al. See ref 5g.
  • 33
    • 0037019658 scopus 로고    scopus 로고
    • Mechanistic hypotheses for isomerization sequences in zirconocene complexes have been reported. See: a
    • Mechanistic hypotheses for isomerization sequences in zirconocene complexes have been reported. See: (a) Chinkov, N.; Majumdar, S.; Marek, I. J. Am Chem. Soc. 2002, 124, 10282-10283.
    • (2002) J. Am Chem. Soc , vol.124 , pp. 10282-10283
    • Chinkov, N.1    Majumdar, S.2    Marek, I.3
  • 38
    • 34547937034 scopus 로고    scopus 로고
    • Formation of products 7 and 8 as single diastereoisomers is surprising as it is known that benzylic organomagnesium species such as 19 are not configurationally stable.
    • Formation of products 7 and 8 as single diastereoisomers is surprising as it is known that benzylic organomagnesium species such as 19 are not configurationally stable.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.