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Volumn 4, Issue 8, 2002, Pages 1367-1370

trans-6-Aminocyclohept-3-enols, a New Designed Polyfunctionalized Chiral Building Block for the Asymmetric Synthesis of 2-Substituted-4-hydroxypiperidines

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CYCLOHEPTANE DERIVATIVE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; HEPTANOL; PIPERIDINE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

EID: 0037129405     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025683x     Document Type: Article
Times cited : (25)

References (35)
  • 1
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    • For reviews on the synthesis of substituted piperidines, see: (a) Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781. (b) Bailey, P. D.; Millwood, P. A.; Smith, P. D. J. Chem. Soc., Chem. Commun. 1998, 633. (c) Leclercq, S.; Daloze, D.; Braekman, J.-C. Org. Prep. Proc. Int. 1996, 28, 499. (d) Wang, C.-L. J.; Wuonola, M. A. Org. Prep. Proc. Int. 1992, 24, 585.
    • (2000) Synthesis , vol.13 , pp. 1781
    • Laschat, S.1    Dickner, T.2
  • 2
    • 21844437339 scopus 로고    scopus 로고
    • For reviews on the synthesis of substituted piperidines, see: (a) Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781. (b) Bailey, P. D.; Millwood, P. A.; Smith, P. D. J. Chem. Soc., Chem. Commun. 1998, 633. (c) Leclercq, S.; Daloze, D.; Braekman, J.-C. Org. Prep. Proc. Int. 1996, 28, 499. (d) Wang, C.-L. J.; Wuonola, M. A. Org. Prep. Proc. Int. 1992, 24, 585.
    • (1998) J. Chem. Soc., Chem. Commun. , pp. 633
    • Bailey, P.D.1    Millwood, P.A.2    Smith, P.D.3
  • 3
    • 0043287627 scopus 로고    scopus 로고
    • For reviews on the synthesis of substituted piperidines, see: (a) Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781. (b) Bailey, P. D.; Millwood, P. A.; Smith, P. D. J. Chem. Soc., Chem. Commun. 1998, 633. (c) Leclercq, S.; Daloze, D.; Braekman, J.-C. Org. Prep. Proc. Int. 1996, 28, 499. (d) Wang, C.-L. J.; Wuonola, M. A. Org. Prep. Proc. Int. 1992, 24, 585.
    • (1996) Org. Prep. Proc. Int. , vol.28 , pp. 499
    • Leclercq, S.1    Daloze, D.2    Braekman, J.-C.3
  • 4
    • 0001003442 scopus 로고
    • For reviews on the synthesis of substituted piperidines, see: (a) Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781. (b) Bailey, P. D.; Millwood, P. A.; Smith, P. D. J. Chem. Soc., Chem. Commun. 1998, 633. (c) Leclercq, S.; Daloze, D.; Braekman, J.-C. Org. Prep. Proc. Int. 1996, 28, 499. (d) Wang, C.-L. J.; Wuonola, M. A. Org. Prep. Proc. Int. 1992, 24, 585.
    • (1992) Org. Prep. Proc. Int. , vol.24 , pp. 585
    • Wang, C.-L.J.1    Wuonola, M.A.2
  • 15
    • 0000490054 scopus 로고
    • Chiral Synthons via Enzyme-Mediated Asymmetrization of Meso-Compounds
    • Dondoni, A., Ed.
    • See, for example: (a) Danieli, B.; Lesma, G.; Passarella, D.; Riva, S. Chiral Synthons via Enzyme-Mediated Asymmetrization of Meso-Compounds. In Advances in the Use of Synthons in Organic Chemistry; Dondoni, A., Ed.; 1993; Vol. 1, pp 143-219. (b) Danieli, B.; Lesma, G.; Passarella, D.; Silvani, A. Curr. Org. Chem. 2000, 4, 231 and references therein.
    • (1993) Advances in the Use of Synthons in Organic Chemistry , vol.1 , pp. 143-219
    • Danieli, B.1    Lesma, G.2    Passarella, D.3    Riva, S.4
  • 16
    • 0034038643 scopus 로고    scopus 로고
    • and references therein
    • See, for example: (a) Danieli, B.; Lesma, G.; Passarella, D.; Riva, S. Chiral Synthons via Enzyme-Mediated Asymmetrization of Meso-Compounds. In Advances in the Use of Synthons in Organic Chemistry; Dondoni, A., Ed.; 1993; Vol. 1, pp 143-219. (b) Danieli, B.; Lesma, G.; Passarella, D.; Silvani, A. Curr. Org. Chem. 2000, 4, 231 and references therein.
    • (2000) Curr. Org. Chem. , vol.4 , pp. 231
    • Danieli, B.1    Lesma, G.2    Passarella, D.3    Silvani, A.4
  • 17
    • 0035847514 scopus 로고    scopus 로고
    • For recent syntheses of 1, see: (a) Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209. (b) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551. (c) Di Nardo, C.; Varela, O. J. Org. Chem. 1999, 64, 6119. (d) Haddad, M.; Larchevêque, M. Tetrahedron: Asymmetry 1999, 10, 4231.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1209
    • Sabat, M.1    Johnson, C.R.2
  • 18
    • 0034611961 scopus 로고    scopus 로고
    • For recent syntheses of 1, see: (a) Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209. (b) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551. (c) Di Nardo, C.; Varela, O. J. Org. Chem. 1999, 64, 6119. (d) Haddad, M.; Larchevêque, M. Tetrahedron: Asymmetry 1999, 10, 4231.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 3551
    • Brooks, C.A.1    Comins, D.L.2
  • 19
    • 0033588134 scopus 로고    scopus 로고
    • For recent syntheses of 1, see: (a) Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209. (b) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551. (c) Di Nardo, C.; Varela, O. J. Org. Chem. 1999, 64, 6119. (d) Haddad, M.; Larchevêque, M. Tetrahedron: Asymmetry 1999, 10, 4231.
    • (1999) J. Org. Chem. , vol.64 , pp. 6119
    • Di Nardo, C.1    Varela, O.2
  • 20
    • 0343852166 scopus 로고    scopus 로고
    • For recent syntheses of 1, see: (a) Sabat, M.; Johnson, C. R. Tetrahedron Lett. 2001, 42, 1209. (b) Brooks, C. A.; Comins, D. L. Tetrahedron Lett. 2000, 41, 3551. (c) Di Nardo, C.; Varela, O. J. Org. Chem. 1999, 64, 6119. (d) Haddad, M.; Larchevêque, M. Tetrahedron: Asymmetry 1999, 10, 4231.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 4231
    • Haddad, M.1    Larchevêque, M.2
  • 24
    • 0442269051 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra after transformation into the (R)- and (S)-MTPA esters (see refs 10 and 9, respectively).
  • 26
    • 0442269050 scopus 로고    scopus 로고
    • Using the Weinreb amide as amination reagent, product formation required 2-3 days and resulted in 21% yield
    • Using the Weinreb amide as amination reagent, product formation required 2-3 days and resulted in 21% yield.
  • 30
    • 0035847514 scopus 로고    scopus 로고
    • A similar strategy, describing the use of a related aldehyde for the synthesis of trans-4-hydroxy-2-pipecolic acid 2 and the antibacterial (-)-SS20846A (26), has been recently reported, see: Johonson, C. R.; Sabat, M. Tetrahedron Lett. 2001, 42, 1209.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1209
    • Johonson, C.R.1    Sabat, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.