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Volumn 53, Issue 21, 1997, Pages 7219-7230

Enantioselective synthesis of new C2-symmetric ferrocenylalkylamines via sonochemical amination of 1-ferrocenylalkyl acetates

Author keywords

[No Author keywords available]

Indexed keywords

FERROCENE DERIVATIVE;

EID: 0030992564     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00407-9     Document Type: Article
Times cited : (45)

References (45)
  • 1
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    • (1989) Chem. Rev. , vol.89 , pp. 1581
    • Whitesell, J.K.1
  • 2
    • 0003643883 scopus 로고
    • Waldmann, H., Ed.: VCH, Weinheim
    • b) Waldmann, H., in Organic Synthesis Highlights II, Waldmann, H., Ed.: VCH, Weinheim 1995, p. 49; and ref. cited therein;
    • (1995) Organic Synthesis Highlights II , pp. 49
    • Waldmann, H.1
  • 5
    • 23744465287 scopus 로고    scopus 로고
    • note
    • 2-axes, are configurationally unstable and therefore non-stereogenic.
  • 15
    • 23744484546 scopus 로고
    • (-)-trans-2,6-Dimethylpiperidine (ent-4, R=Me) was obtained either by (partial) resolution: a) Hill, R. K.; Morgan, J. W. J. Org. Chem. 1966, 31, 3541;
    • (1966) J. Org. Chem. , vol.31 , pp. 3541
    • Hill, R.K.1    Morgan, J.W.2
  • 16
    • 0010501593 scopus 로고
    • or as part of a diastereomeric mixture by cyclization of (-)-1-methylhexylamine: b) Perrone, R.; Tortorella, V. Tetrahedron 1978, 34, 2533;
    • (1978) Tetrahedron , vol.34 , pp. 2533
    • Perrone, R.1    Tortorella, V.2
  • 19
    • 0001426637 scopus 로고    scopus 로고
    • b) Togni, A. Angew. Chem. 1996, 108, 1581 and ref. cited therein.
    • (1996) Angew. Chem. , vol.108 , pp. 1581
    • Togni, A.1
  • 23
    • 0040755377 scopus 로고
    • A mixture of the racemic compound rac-5 and its meso diastereomer 16 has been prepared previously: Butler, I. R.; Cullen, W. R. Can. J. Chem. 1983, 61, 2354.
    • (1983) Can. J. Chem. , vol.61 , pp. 2354
    • Butler, I.R.1    Cullen, W.R.2
  • 25
    • 0000560997 scopus 로고
    • Togni, A.; Hayashi, T., Eds.: VCH Weinheim chapter 4
    • See, for instance: Wagner, G.; Herrmann, R. in Togni, A.; Hayashi, T., Eds.: Ferrocenes, VCH Weinheim 1995, chapter 4, p. 173.
    • (1995) Ferrocenes , pp. 173
    • Wagner, G.1    Herrmann, R.2
  • 33
    • 23744469317 scopus 로고    scopus 로고
    • 9c
    • 9c.
  • 36
    • 23744439515 scopus 로고    scopus 로고
    • note
    • The optical purity of alcohol 13 was routinely determined by analytical HPLC on a Daicel Chiralcel OJ-column (i-PrOH / hexane = 15:85).
  • 37
    • 0004063331 scopus 로고
    • Springer Verlag, Berlin Heidelberg
    • For the use of ultrasound in organic synthesis, see for instance: Ley, S.; Low, C.M.R. Ultrasound in Synthesis, Springer Verlag, Berlin Heidelberg 1989.
    • (1989) Ultrasound in Synthesis
    • Ley, S.1    Low, C.M.R.2
  • 38
    • 23744487424 scopus 로고    scopus 로고
    • note
    • The fact that the product was obtained as a pure diastereomer directly proves the high enantiomeric purity (> 98 % ee) of the starting material(s) and the product.
  • 39
    • 0000884787 scopus 로고
    • For the use of AcOH as solvent for substitution reactions of ferrocenyl derivatives, see: Barbaro, P.; Togni, A. Organometallics 1995, 14, 3570.
    • (1995) Organometallics , vol.14 , pp. 3570
    • Barbaro, P.1    Togni, A.2
  • 42
    • 23744503045 scopus 로고    scopus 로고
    • note
    • 8a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.