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Volumn 75, Issue 5, 2010, Pages 1748-1751

Facile syntheses of enantiopure 3-hydroxypiperidine derivatives and 3-hydroxypipecolic acids

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYPIPECOLIC ACID; CHEMICAL EQUATIONS; CYCLOHYDROCARBONYLATION; ENANTIOPURE; FACILE SYNTHESIS; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

EID: 77949298327     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902324h     Document Type: Article
Times cited : (26)

References (37)
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  • 4
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    • For recent study of azasugar inhibition, see: a
    • For recent study of azasugar inhibition, see: (a) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1999, 38, 750-770.
    • (1999) Angew. Chem., Int. Ed , vol.38 , pp. 750-770
    • Heightman, T.D.1    Vasella, A.T.2
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    • For recent reviews, see: a
    • For recent reviews, see: (a) Butters, T. D.; Dwek, R. A.; Platt, F. M. Chem. Rev. 2000, 12, 4683-4696.
    • (2000) Chem. Rev , vol.12 , pp. 4683-4696
    • Butters, T.D.1    Dwek, R.A.2    Platt, F.M.3
  • 7
    • 11944256494 scopus 로고
    • b) Sinnott, M. L. Chem. Rev. 1990, 90, 1171-1202.
    • (1990) Chem. Rev , vol.90 , pp. 1171-1202
    • Sinnott, M.L.1
  • 11
    • 77949299075 scopus 로고    scopus 로고
    • Garner, P.; Park, J.-M. In Organic Syntheses; Wiley: New York, 1998; Collect. IX, p 300.
    • b) Garner, P.; Park, J.-M. In Organic Syntheses; Wiley: New York, 1998; Collect. Vol. IX, p 300.
  • 15
    • 84962440205 scopus 로고    scopus 로고
    • For recent reviews of cyclohydrocarbonylation, see: a, Hiyama, T, Ojima, I, Eds, Elsevier: Oxford, Chapter 11.15, pp
    • For recent reviews of cyclohydrocarbonylation, see: (a) Ojima, I.; Commandeur, C.; Chiou, W.-H. In Comprehensive Organometallic Chemistry-III; Hiyama, T., Ojima, I., Eds.; Elsevier: Oxford, 2006; Chapter 11.15, ;pp 511-556.
    • (2006) Comprehensive Organometallic Chemistry-III , pp. 511-556
    • Ojima, I.1    Commandeur, C.2    Chiou, W.-H.3
  • 17
    • 77949283823 scopus 로고    scopus 로고
    • A DFT-B3LYP/6-31G* calculation by Spartan 08 indicated 5a is more stable than 6a by 8.9 kcal/mol in vacuo and by 8.2 kcal/mol in toluene using the SM8 model.
    • A DFT-B3LYP/6-31G* calculation by Spartan 08 indicated 5a is more stable than 6a by 8.9 kcal/mol in vacuo and by 8.2 kcal/mol in toluene using the SM8 model.
  • 18
    • 77949282944 scopus 로고    scopus 로고
    • We did an experiment to confirm the isomerization: treatment of pure amidal 5 in the mixture solution of ethyl acetate and chloroform, v/v, 1:1 containing silica gel resulted in the formation of encarbamate 6a (5a/6a ∼ 1:1) by 1H NMR analysis
    • 1H NMR analysis.
  • 19
  • 23
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    • For recent syntheses of 3-hydroxypipecolic acids, see: a
    • For recent syntheses of 3-hydroxypipecolic acids, see: (a) Greek, C.; Ferreira, F.; Genêt, J. P. Tetrahedron Lett. 1996, 37, 2031-2034.
    • (1996) Tetrahedron Lett , vol.37 , pp. 2031-2034
    • Greek, C.1    Ferreira, F.2    Genêt, J.P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.