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Volumn 32, Issue 4, 1993, Pages 568-570

Asymmetric Synthesis and Highly Diastereoselective ortho‐Lithiation of Ferrocenyl Sulfoxides. Application to the Synthesis of Ferrocenyl Derivatives with Planar Chirality

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Indexed keywords


EID: 33748231903     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.199305681     Document Type: Article
Times cited : (210)

References (25)
  • 7
    • 84989563158 scopus 로고    scopus 로고
    • Sulfite 5 can be obtained in two steps from ethyl (S)‐lactate [3,5] and is also commercially available at Aldrich Co.
  • 12
    • 84989582993 scopus 로고    scopus 로고
    • w = 0.078, G.O.F. = 1.62. The analysis confirms the (S) configuration at sulfur (agreement factors for the enantiomeric structure: R = 0.054, R = 0.085, G.O.F. = 1.755). Further details of the crystal structure investigation are available on request from the Director of the Cambridge Crystallographic Data Centre, 12 Union Road, GB‐Cambridge CB21EZ (UK), on quoting the full journal citation.
  • 14
    • 84989543076 scopus 로고    scopus 로고
    • 1H NMR spectroscopy (p‐tolyl Me group). For comparison, the epimer of 2a was prepared by the method described in ref. [11] for inversion of configuration at the sulfur of sulfoxides.
  • 16
    • 84989543093 scopus 로고    scopus 로고
    • For example, oxidation of 11 provides the sulfone which is activated for deprotonation and stannylation on the second ortho position. In that way tert‐butyl [1‐methyl‐5‐(tributylstannyl)‐ferrocenyl]sulfone 3a prepared Scheme 2
  • 18
    • 84989563166 scopus 로고    scopus 로고
    • Reductive cleavage for replacing sulfinyl or sulfonyl groups by hydrogen atoms is a well‐known process, for example see refs. [14, 15]. The substitution of vinyl and aryl sulfoxides is less common, but still possible, especially when the reaction is catalyzed by a transition metal complex [16, 17].
  • 23
    • 84989576165 scopus 로고    scopus 로고
    • A related diastereoselective ortho‐lithiation of chromium arene complexes has been recently described [19, 20].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.