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Volumn 44, Issue 3, 2003, Pages 527-530

Efficient access to chiral trans-2,6-dialkyl-1,2,5,6-tetrahydropyridines via allylation of chiral imines and ring-closing metathesis

Author keywords

[No Author keywords available]

Indexed keywords

3 PIPERIDEINE DERIVATIVE; ALCOHOL DERIVATIVE; ALDEHYDE; IMINE;

EID: 0037433951     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02586-8     Document Type: Article
Times cited : (25)

References (34)
  • 4
    • 0033709712 scopus 로고    scopus 로고
    • For a review on asymmetric synthesis of piperidines, see: (b) Laschat, S.; Dickner, T. Synthesis 2000, 1781-1813.
    • (2000) Synthesis , pp. 1781-1813
    • Laschat, S.1    Dickner, T.2
  • 8
    • 84944032302 scopus 로고    scopus 로고
    • Fowler, F. W. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Ree, C. W.; Eds. Pergamon Press: London, 1984; Vol. 2, Part 2A, pp. 365-394.
  • 17
    • 0012121486 scopus 로고    scopus 로고
    • note
    • All enantiomeric excesses were determined by HPLC with a chiral column (Chiracel OD-H 0.46×15 cm). For (E)-2 separation conditions: elution with a mixture of hexane/i-PrOH 99:1 v/v; flow rate: 0.5 ml/min; retention time 14.1 min for minor enantiomer and 15.1 min for major.
  • 21
    • 0012161340 scopus 로고    scopus 로고
    • note
    • Other allylic organometallic reagents (Zn, Cu, Ce) were also tried, but no reaction (with Cu and Zn) or lower yield with similar diastereoselectivity (with Ce) were noted.
  • 22
    • 0012195247 scopus 로고    scopus 로고
    • note
    • +) 262.1596, found 262.1593.
  • 24
    • 0038106171 scopus 로고    scopus 로고
    • For reviews on this fields, see: (b) Bloch, R. Chem. Rev. 1998, 98, 1407-1438;
    • (1998) Chem. Rev. , vol.98 , pp. 1407-1438
    • Bloch, R.1
  • 25
    • 0036251136 scopus 로고    scopus 로고
    • For reviews on this fields, see: (c) Alvaro, G.; Savoia, D. Synlett 2002, 651-673.
    • (2002) Synlett , pp. 651-673
    • Alvaro, G.1    Savoia, D.2
  • 29
    • 0032580376 scopus 로고    scopus 로고
    • For reviews on the RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450;
    • (1998) Tetrahedron , vol.54 , pp. 4413-4450
    • Grubbs, R.H.1    Chang, S.2
  • 33
    • 0012126160 scopus 로고    scopus 로고
    • note
    • The trans configuration assignment for compound 8a is consistent with the conversion of this intermediate into known deprotected trans-2,6-dialkyl-tetrahydropyridine derivative and comparison of the NMR data reported in the literature, see: Pernerstorfer, J.; Schuster, M.; Blechert, S. Synthesis 1999, 138-144. The trans configuration of 8c was attributed by conversion of the minor cis isomer 8c into known deprotected cis-2,6-dialkyl-piperidine, see: Åhman, J.; Somfai, P. Tetrahedron 1995, 51, 9747-9756.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.