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Volumn , Issue 2, 2005, Pages 347-356

N-ferrocenyl-substituted planar-chiral N-heterocyclic carbenes and their PdII complexes

Author keywords

Carbene ligands; Chirality; Ferrocenes; Nitrogen heterocycles; Palladium

Indexed keywords

ELECTRONIC PROPERTIES; NITROGEN; ORGANIC COMPOUNDS; PALLADIUM COMPOUNDS; POTASSIUM COMPOUNDS;

EID: 13844299853     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200400691     Document Type: Article
Times cited : (72)

References (44)
  • 17
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    • note
    • An N,N′-dicyclophane-substituted carbene analogous to 1a and a related Rh complex have been reported recently: Y. D. Ma, C. Song, C. Q. Ma, Z. J. Sun, Q. Chai, M. B. Andrus, Angew. Chem. Int. Ed. 2003, 42, 5871. Interesting results were obtained in the asymmetric addition of arylboron reagents to enones (ee up to 98%).
  • 18
    • 85163229995 scopus 로고    scopus 로고
    • note
    • -.
  • 23
    • 85163227966 scopus 로고    scopus 로고
    • note
    • Aminoferrocene was first synthesized by Nesmeyanov (ref.[25]), who treated lithiated ferrocene with the O-benzyl ether of hydroxylamine and isolated the product in 25% yield. In the same year Arimoto and Haven synthesized aminoferrocene (ref.[26]) from ferrocenecarboxylic acid by using the Curtius synthetic strategy, but the overall yield was lower than 20%. Other approaches including Beckmann rearrangement from the oxime proved fruitless. Lehner and Schlögl, in 1970 (ref.[27]), reported the synthesis of planar-chiral (R)-1-amino-2-methylferrocene in 26% yield from (R)-2-methylferrocenecarboxylic acid by a modified procedure and determined its absolute configuration. The approach presented here differs from Schlögl's approach in various reaction conditions such as temperatures, solvents, the activation of the carboxylic acid and the fact that the sequence was performed in two steps in 82% yield. A recent example of a high yielding (80%) Curtius degradation sequence leading to achiral aminoferrocene can be found in ref.[28]
  • 24
    • 0001695276 scopus 로고
    • Ferrocene compounds containing heteroelements
    • (Eds.: A. Togni, T. Hayashi), Wiley-VCH, Weinheim
    • M. Herberhold, "Ferrocene Compounds Containing Heteroelements", in Ferrocenes (Eds.: A. Togni, T. Hayashi), Wiley-VCH, Weinheim, 1995.
    • (1995) Ferrocenes
    • Herberhold, M.1
  • 26
    • 4243255874 scopus 로고
    • A. N. Nesmeyanov, E. G. Perevalova, R. V. Golovnya, L. S. Shilovtseva, Dokl. Akad. Nauk. SSSR 1955, 102, 535; Chem. Abstr. 1956, 50, 4925g.
    • (1956) Chem. Abstr. , vol.50
  • 35
    • 85163229635 scopus 로고    scopus 로고
    • note
    • The amines 9a and 9b could have been produced directly from the isocyanate by adding water instead of benzylic alcohol but the purification and storage of the air-stable carbamate 8 proved to be more convenient.
  • 37
    • 85163235610 scopus 로고    scopus 로고
    • note
    • The acetal was synthesized instead of the aldehyde in order to prevent oxazole formation in the following cyclization step.
  • 38
    • 85163232730 scopus 로고    scopus 로고
    • PhD thesis Nr. 15041, ETH Zürich
    • D. Broggini, PhD thesis Nr. 15041, ETH Zürich, 2003.
    • (2003)
    • Broggini, D.1
  • 40
    • 85163234026 scopus 로고    scopus 로고
    • note
    • PH(olefinic) = 1.2 Hz.
  • 43
    • 85163225617 scopus 로고    scopus 로고
    • note
    • 2, 15% of 12a and 1.5 equiv. of NaOtBu in 1,4-dioxane at 50 °C for 26 h gave (+)-1,3-dimethyl-3- (1-naphthyl)oxindole in the mentioned yield and ee. When 16a was used, the ee values and activity were slightly lower.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.