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Volumn 3, Issue 21, 2001, Pages 3257-3260

Unprecedented oxidation of a phenylglycinol-derived 2-pyridone: Enantioselective synthesis of polyhydroxypiperidines

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYPYRIDINE; 2-HYDROXYPYRIDINE; DRUG DERIVATIVE; ENZYME INHIBITOR; GLYCINE; GLYCOSIDASE; PHENYLGLYCINOL; PIPERIDINE DERIVATIVE; PYRIDONE DERIVATIVE;

EID: 0035909621     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016418z     Document Type: Article
Times cited : (44)

References (43)
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  • 24
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    • (j) For the use of related chiral bicyclic phenylglycinol-derived 2-cyanopiperidines, see: Husson, H.-P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383.
    • (1999) Chem. Soc. Rev. , vol.28 , pp. 383
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  • 26
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    • 13C NMR), analytical, and/or HRMS data were obtained for all new compounds
    • 13C NMR), analytical, and/or HRMS data were obtained for all new compounds.
  • 27
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    • 4 and NMO, DMD or UHP led only to the recovery of the starting material. Similarly, the O-silyl protected (TBDMS) lactam derived from 1 was recovered unchanged after exposure to m-CPBA
    • 4 and NMO, DMD or UHP led only to the recovery of the starting material. Similarly, the O-silyl protected (TBDMS) lactam derived from 1 was recovered unchanged after exposure to m-CPBA.
  • 28
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    • note
    • -3.
  • 29
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    • It has been demonstrated that related cis-3,8a bicyclic lactams equilibrate to the trans isomers; see ref 6f
    • It has been demonstrated that related cis-3,8a bicyclic lactams equilibrate to the trans isomers; see ref 6f.
  • 30
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    • Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart
    • (a) Schwesinger, R.; Willaredt, J.; Bauer, T. In Stereoselective Synthesis (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 8, pp 4599-4697.
    • (1996) Stereoselective Synthesis (Houben-weyl) , vol.8 , pp. 4599-4697
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    • and references therein
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  • 32
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    • (a) For the Elbs peroxydisulfate oxidation of 2-pyridone to 5-hydroxy-2-pyridone, see: Behrman, E. J.; Pitt, B. M. J. Am. Chem. Soc. 1958, 80, 3717.
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    • (b) For the dioxygenase-catalyzed cis-dihydroxylation of N-methyl-2-pyridone, see: Modyanova, L.; Azerard, R. Tetrahedron Lett. 2000, 41, 3865.
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    • Modyanova, L.1    Azerard, R.2
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    • For previous enantioselective syntheses of 3-hydroxypiperidine, see: (a) Huh, N.; Thompson, C. M. Tetrahedron 1995, 51, 5935.
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    • Huh, N.1    Thompson, C.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.