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Volumn 64, Issue 27, 2008, Pages 6252-6262

Functionalized analogues of Tröger's base: scope and limitations of a general synthetic procedure and facile, predictable method for the separation of enantiomers

Author keywords

Anilines; Enantioseparation; Tr ger's base; Whelk O1

Indexed keywords

ANILINE DERIVATIVE; DIAMINE DERIVATIVE; PARAFORMALDEHYDE; TROGER BASE;

EID: 44349106975     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.04.111     Document Type: Article
Times cited : (51)

References (82)
  • 56
    • 44349142785 scopus 로고    scopus 로고
    • note
    • 2N group into a very strong acceptor, which would deactivate the aromatic ring toward electrophilic substitutions. However, there is always some free amine in equilibrium with an ammonium cation.
  • 68
    • 44349087011 scopus 로고    scopus 로고
    • note
    • The synthesis of (±)-2e was very recently reported by Lützen and co-workers, Ref. 9. We thank Prof. A. Lützen and Dr. U. Kiehne for the helpful discussion concerning the variation of conditions in this reaction.
  • 69
    • 44349115614 scopus 로고    scopus 로고
    • note
    • 3COOH in one portion without cooling resulted in an exothermic reaction that produced a tarry, dark material and only traces of the desired Tröger's base analogue.
  • 70
    • 44349146702 scopus 로고    scopus 로고
    • note
    • Di- or tetramethyl derivatives (±)-3c-f should be more reactive toward electrophilic substitution than (±)-1b. In a preliminary experiment, we confirmed a much higher reactivity of (±)-3c compared to (±)-1b in the electrophilic bromination. This study is currently in progress and will be published in due course.
  • 78
    • 44349117988 scopus 로고    scopus 로고
    • Regis Technologies, Morton Grove, USA
    • Chiral Application Guide VI (2006), Regis Technologies, Morton Grove, USA. p 15. Available online at www.registech.com/chiral/
    • (2006) Chiral Application Guide VI


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.