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Volumn , Issue 4, 2010, Pages 567-570

Asymmetric synthesis of piperidines and octahydroindolizines

Author keywords

coniceine; Asymmetric synthesis; Coniine; Lithium amides; Piperidines

Indexed keywords

AMIDE; CONIINE; DELTA CONICIENE; INDOLIZINE DERIVATIVE; LITHIUM; LITHIUM AMIDE; OCTAHYDROINDOLIZINE DERIVATIVE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77955356947     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/S-0029-1219346     Document Type: Article
Times cited : (29)

References (41)
  • 23
    • 77955402345 scopus 로고    scopus 로고
    • ξ-Hydroxy-α,β-unsaturated ester 13 was prepared in 55% yield [96:4 E/Z ratio] via the one-pot treatment of δ-valerolactone with DIBAL-H, tert-butyl 2-(diethoxy-phosphoryl)acetate and BuLi at-78 °C. See ref. 9 for details
    • ξ-Hydroxy-α,β-unsaturated ester 13 was prepared in 55% yield [96:4 E/Z ratio] via the one-pot treatment of δ-valerolactone with DIBAL-H, tert-butyl 2-(diethoxy-phosphoryl)acetate and BuLi at-78 °C. See ref. 9 for details.
  • 28
    • 77955379788 scopus 로고    scopus 로고
    • For a related example, see ref. 11a
    • For a related example, see ref. 11a.
  • 29
    • 37049072079 scopus 로고
    • β-Amino aldehydes are known to be unstable with respect to retro-Michael reactions; see
    • β-Amino aldehydes are known to be unstable with respect to retro-Michael reactions; see: Carruthers, W.; Moses, R. C. J. Chem. Soc., Perkin Trans. 1 1988, 2251.
    • (1988) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 2251
    • Carruthers, W.1    Moses, R.C.2
  • 30
    • 77955343389 scopus 로고    scopus 로고
    • B]
    • B].
  • 32
    • 77955346854 scopus 로고    scopus 로고
    • +: 126.1283; found: 126.1278
    • +: 126.1283; found: 126.1278.
  • 34
    • 0028953345 scopus 로고
    • Within this area, Monterrey et al. have shown that alkylation of N-Cbz protected piperidin-2-yl-acetates with ethyl bromoacetate can lead to successful ring closure by removal of the N-Cbz protecting group in a tandem hydrogenolysis-hydrogenation step to give the corresponding hexahydro-indolizin- 3-one; see
    • Within this area, Monterrey et al. have shown that alkylation of N-Cbz protected piperidin-2-yl-acetates with ethyl bromoacetate can lead to successful ring closure by removal of the N-Cbz protecting group in a tandem hydrogenolysis-hydrogenation step to give the corresponding hexahydro-indolizin- 3-one; see: Monterrey, I. M. G.; González-Muñiz, R.; Herranz, R.; Garcia-López, M. T. Tetrahedron 1995, 51, 2729.
    • (1995) Tetrahedron , vol.51 , pp. 2729
    • Monterrey, I.M.G.1    González-Muñiz, R.2    Herranz, R.3    Garcia-López, M.T.4
  • 35
    • 37049071174 scopus 로고
    • The anti-configuration of the alkylation was assigned on the basis of the established preferential anti-alkylations of lithium β-amino enolates, see
    • The anti-configuration of the alkylation was assigned on the basis of the established preferential anti-alkylations of lithium β-amino enolates, see: (a) Davies, S. G.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 1129.
    • (1994) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 1129
    • Davies, S.G.1    Walters, I.A.S.2
  • 37
    • 77955405957 scopus 로고    scopus 로고
    • +
    • +.
  • 38
    • 0025344784 scopus 로고
    • Both diastereomers of l-(hydroxymethyl)octahydro-indolizidine (40) have previously been reported, see
    • Both diastereomers of l-(hydroxymethyl)octahydro-indolizidine (40) have previously been reported, see: (a) Nagao, Y.; Dai, W.; Ochiai, M.; Tsukagoshi, S.; Fujitalc, E. J. Org. Chem. 1990, 55, 1148.
    • (1990) J. Org. Chem. , vol.55 , pp. 1148
    • Nagao, Y.1    Dai, W.2    Ochiai, M.3    Tsukagoshi, S.4    Fujitalc, E.5
  • 41
    • 77955412067 scopus 로고    scopus 로고
    • Some discrepancies exist between the reported characterisation data for 40 and its epimer; these will be highlighted in a forthcoming publication from this laboratory. However, our synthesis unambiguously confirms the relative and absolute configuration of 40
    • Some discrepancies exist between the reported characterisation data for 40 and its epimer; these will be highlighted in a forthcoming publication from this laboratory. However, our synthesis unambiguously confirms the relative and absolute configuration of 40.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.