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Volumn 3, Issue 6, 2006, Pages 470-476

Intramolecular carbolithiation of aromatic N-allyl-N-(2-lithioallyl)amines: Reinvestigation of the mechanism and synthesis of functionalized pyrrolidines

Author keywords

5 exo cyclizations; Carbolithiation reactions; Organolithiums; Pyrrolidines

Indexed keywords


EID: 33746161966     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806777828420     Document Type: Article
Times cited : (4)

References (27)
  • 4
    • 33746123843 scopus 로고    scopus 로고
    • Rappoport, Z.; Marek, I., Eds.; John Wiley & Sons: West Sussex Ch. 4
    • d) Fananás, F.J.; Sanz, R. In The Chemistry of Organolithium Compounds, Rappoport, Z.; Marek, I., Eds.; John Wiley & Sons: West Sussex, 2006; Vol. 2; Ch. 4, pp. 295-379.
    • (2006) The Chemistry of Organolithium Compounds , vol.2 , pp. 295-379
    • Fananás, F.J.1    Sanz, R.2
  • 5
    • 0036499897 scopus 로고    scopus 로고
    • For a review, see The preparation of pyrrolidines by carbolithiation reactions of N-homoallyl α-amino-organolithiums has been extensively studied by Coldham and coworkers: Ashweek, N.J.; Coldham, I.; Snowden, D.J.; Vennall, G.P. Chem. Eur. J. 2002, 8, 195-207 and references cited therein
    • For a review, see: Mealy, M.J.; Bailey, W.F. J. Organomet. Chem. 2002, 646, 59-67. The preparation of pyrrolidines by carbolithiation reactions of N-homoallyl α-amino-organolithiums has been extensively studied by Coldham and coworkers: Ashweek, N.J.; Coldham, I.; Snowden, D.J.; Vennall, G.P. Chem. Eur. J. 2002, 8, 195-207 and references cited therein.
    • (2002) Organomet. Chem. , vol.646 , pp. 59-67
    • Mealy, M.J.1    Bailey, W.F.J.2
  • 20
    • 33746121537 scopus 로고    scopus 로고
    • At this temperature the carbolithiation reaction needed ca. 12 h to get completion
    • At this temperature the carbolithiation reaction needed ca. 12 h to get completion.
  • 21
    • 0041378607 scopus 로고
    • Vinyllithium compounds bearing aryl substituents are known to undergo facile cis-trans isomerization, and kinetic studies on the rate of these isomerizations have been reported. See: a)
    • Vinyllithium compounds bearing aryl substituents are known to undergo facile cis-trans isomerization, and kinetic studies on the rate of these isomerizations have been reported. See: a) Hunter, D.H.; Cram, D.J. J. Am. Chem. Soc. 1964,86, 5478-5490.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 5478-5490
    • Hunter, D.H.1    Cram, D.J.2
  • 23
    • 33746117273 scopus 로고    scopus 로고
    • Evolution of 7c to room temperature in order to favor the formation of 9c gave rise to a complex mixture of products
    • Evolution of 7c to room temperature in order to favor the formation of 9c gave rise to a complex mixture of products.
  • 24
    • 33845278764 scopus 로고
    • Only 1,2-disubstituted olefins in which the initially formed alkyllithium product is substituted with a moderately activating group or with a leaving group in a β-position are useful substrates for this kind of carbocyclizations, see: a)
    • Only 1,2-disubstituted olefins in which the initially formed alkyllithium product is substituted with a moderately activating group or with a leaving group in a β-position are useful substrates for this kind of carbocyclizations, see: a) Broka, C.A.; Lee, W.J.; Shen, T. J. Org. Chem. 1988, 53, 1336-1338.
    • (1988) J. Org. Chem. , vol.53 , pp. 1336-1338
    • Broka, C.A.1    Lee, W.J.2    Shen, T.3
  • 26
    • 33746172654 scopus 로고    scopus 로고
    • note
    • 16BrN: 265.0466, found: 265.0473.
  • 27
    • 33746107993 scopus 로고    scopus 로고
    • note
    • 2 position and so, 9a can not be obtained.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.