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Volumn 29, Issue 1, 2010, Pages 199-204

Iron(0) tricarbonyl complexes of microbially derived cyclohexadiene ligands containing quaternary stereocenters

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID; CYCLOHEXADIENES; MICROBIAL OXIDATION; OXIDATIVE MODIFICATION; QUATERNARY CENTERS; QUATERNARY STEREOCENTERS; TRICARBONYL COMPLEXES;

EID: 73649140240     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9009069     Document Type: Article
Times cited : (17)

References (79)
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    • Iron complexes in organic chemistry
    • Plietker, B, Ed, Wiley-VCH: Weinheim, Germany
    • (a) Bauer, I.; Knölker, H.-J. Iron complexes in organic chemistry. In Iron Catalysis in Organic Chemistry; Plietker, B., Ed.; Wiley-VCH: Weinheim, Germany, 2008; pp 1-27.
    • (2008) Iron Catalysis in Organic Chemistry , pp. 1-27
    • Bauer, I.1    Knölker, H.-J.2
  • 7
    • 0001524228 scopus 로고
    • Acyclic Diene Tricarbonyliron Complexes in Organic Synthesis
    • Liebskind, L. S, Ed, JAI Press: Greenwich, CT
    • (f) Grée, R.; Lellouche, J. P. Acyclic Diene Tricarbonyliron Complexes in Organic Synthesis. In Advances in Metal-Organic Chemistry; Liebskind, L. S., Ed.; JAI Press: Greenwich, CT, 1995; pp 129-273.
    • (1995) Advances in Metal-Organic Chemistry , pp. 129-273
    • Grée, R.1    Lellouche, J.P.2
  • 29
    • 84890995246 scopus 로고    scopus 로고
    • Polyfunctional electrophilic multihapto-organometallics for organic synthesis
    • For discussions of this nomenclature as applied to tricarbonyliron complexes, see: a, Knochel, P, Ed, Wiley-VCH: Weinheim, Germany
    • For discussions of this nomenclature as applied to tricarbonyliron complexes, see: (a) Stephenson, G. R. Polyfunctional electrophilic multihapto-organometallics for organic synthesis. In Handbook of Functionalised Organometallics; Knochel, P., Ed.; Wiley-VCH: Weinheim, Germany, 2005; pp 569-626.
    • (2005) Handbook of Functionalised Organometallics , pp. 569-626
    • Stephenson, G.R.1
  • 30
  • 31
    • 38749127220 scopus 로고    scopus 로고
    • For recent examples, see: c
    • For recent examples, see: (c) Roe, C.; Stephenson, G. R. Org. Lett. 2008, 10,189.
    • (2008) Org. Lett , vol.10 , pp. 189
    • Roe, C.1    Stephenson, G.R.2
  • 58
    • 0000391897 scopus 로고    scopus 로고
    • Swern oxidation and use of Dess-Martin periodinane were unsuccessful. There exists a sole report in the literature of the successful use of a chromium(VI) reagent to effect oxidation in the context of tricarbonyl(diene) iron alcohols: Birch, A. J.; Kelly, L. F.; Weerasuria, D. V. J. Org. Chem. 1988, 53, 278. We thus employed chromium trioxide as oxidant, obtaining 11 in only 9% yield; use of pyridinium chlorochromate afforded a marginal improvement (12%). Parikh-Doering oxidation was similarly low-yielding (7%).
    • Swern oxidation and use of Dess-Martin periodinane were unsuccessful. There exists a sole report in the literature of the successful use of a chromium(VI) reagent to effect oxidation in the context of tricarbonyl(diene) iron alcohols: Birch, A. J.; Kelly, L. F.; Weerasuria, D. V. J. Org. Chem. 1988, 53, 278. We thus employed chromium trioxide as oxidant, obtaining 11 in only 9% yield; use of pyridinium chlorochromate afforded a marginal improvement (12%). Parikh-Doering oxidation was similarly low-yielding (7%).
  • 76
    • 73649091868 scopus 로고    scopus 로고
    • The corresponding protons in the complex lacking the ester (2, R = H) have not been assigned unambiguously.
    • The corresponding protons in the complex lacking the ester (2, R = H) have not been assigned unambiguously.


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