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Volumn , Issue 12, 2008, Pages 1840-1844

One-pot, three-component, highly diastereoselective metal-free synthesis of 2,3,4,5-tetrasubstituted pyrrolidines

Author keywords

Cycloaddition; Metal free; Pyrrolidines; Stereoselectivity; Three component

Indexed keywords

PYRROLIDINE DERIVATIVE;

EID: 48349102069     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078566     Document Type: Article
Times cited : (19)

References (30)
  • 1
    • 48349085347 scopus 로고    scopus 로고
    • ICREA Researcher at University of Barcelona
    • ICREA Researcher at University of Barcelona.
  • 2
    • 38349178582 scopus 로고    scopus 로고
    • For an excellent review of enamine catalysis, see
    • (a) For an excellent review of enamine catalysis, see: Erkkila, A.; Majander, I.; Pihko, P. Chem. Rev. 2007, 107, 5416.
    • (2007) Chem. Rev , vol.107 , pp. 5416
    • Erkkila, A.1    Majander, I.2    Pihko, P.3
  • 3
    • 33745715054 scopus 로고    scopus 로고
    • For an excellent review of asymmetric synthesis enabled by metal-free catalysis, see
    • (b) For an excellent review of asymmetric synthesis enabled by metal-free catalysis, see: Lelais, G.; MacMillan, D. W. C. Aldrichimica Acta 2006, 3, 79.
    • (2006) Aldrichimica Acta , vol.3 , pp. 79
    • Lelais, G.1    MacMillan, D.W.C.2
  • 4
    • 34250613134 scopus 로고    scopus 로고
    • For an excellent review of Michael additions, see
    • (c) For an excellent review of Michael additions, see: Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701.
    • (2007) Eur. J. Org. Chem , pp. 1701
    • Tsogoeva, S.B.1
  • 29
    • 48349098823 scopus 로고    scopus 로고
    • Chloroform was bought from Aldrich and was used as received
    • Chloroform was bought from Aldrich and was used as received.
  • 30
    • 48349096366 scopus 로고    scopus 로고
    • Typical Experimental Procedure for the Three-Component Synthesis of Pyrrolidine Derivatives To a stirred solution of aldehyde 3 (0.375 mmol, 1.5 equiv) in CHCl3 (0.5 mL) at r.t, diethyl 2-aminomalonate (2a, 0.375 mmol, 1.5 equiv) was added. The reaction was stirred at r.t. for 30 min and then nitroalkene 1 was added. The reaction was then stirred at r.t. overnight. Next the crude was purified by silica gel column chromatography to afford the pyrrolidine derivative 4. Compound 4d: colorless oil. 1H NMR (400 MHz, CDCl3, δ, 7.48-7.44 (m, 2 H, 7.33-7.28 (m, 7 H, 5.58 (dd, J, 6.8, 8.0 Hz, 1 H, 5.46 (d, J, 8.4 Hz, 1 H, 5.12 (d, J, 7.2 Hz, 1 H, 4.42-4.21 (m, 2 H, 3.91 (q, J, 7.6 Hz, 1 H, 3.46 (q, J, 7.6 Hz, 1 H, 1.29 (t, J, 7.6 Hz, 3 H, 0.78 (t, J, 7.6 Hz, 3 H, 13C NMR 100 MHz, CDCl3, δ, 171.1, 168.4, 135.7, 134.9
    • 3): δ = 171.1, 168.4, 135.7, 134.9, 132.4, 131.6, 130.9, 128.9, 128.7, 128.6, 128.3, 122.9, 93.5, 75.9, 63.8, 62.2, 62.0, 51.9, 14.0, 13.3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.