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Volumn 70, Issue 24, 2005, Pages 10182-10185

Stereoselective total synthesis of cis- and trans-3-hydroxypipecolic acid

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYST SELECTIVITY; CHELATION; MOLECULAR STRUCTURE; REDUCTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 28044433662     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051725u     Document Type: Article
Times cited : (54)

References (43)
  • 1
    • 0001867685 scopus 로고
    • The pyridine and piperidine alkaloids: Chemistry and pharmacology
    • Pelletier, S. W., Ed.; Wiley-Interscience: New York
    • (a) Fodor, G. B.; Colasanti, B. The Pyridine and Piperidine Alkaloids: Chemistry and Pharmacology. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1985; Vol. 3, pp 1.
    • (1985) Alkaloids: Chemical and Biological Perspectives , vol.3 , pp. 1
    • Fodor, G.B.1    Colasanti, B.2
  • 2
    • 77957037489 scopus 로고    scopus 로고
    • Pyridine and piperidine alkaloids: An update
    • Pelletier, S. W., Ed.; Pergamon: Oxford
    • (b) Schneider, M. J. Pyridine and Piperidine Alkaloids: An Update. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, 1996; Vol. 10, p 155.
    • (1996) Alkaloids: Chemical and Biological Perspectives , vol.10 , pp. 155
    • Schneider, M.J.1
  • 13
    • 11844290668 scopus 로고    scopus 로고
    • For some recent synthetic studies, see: (a) Kumar, P.; Bodas, M. S. J. Org. Chem. 2005, 70, 360.
    • (2005) J. Org. Chem. , vol.70 , pp. 360
    • Kumar, P.1    Bodas, M.S.2
  • 31
    • 0345871953 scopus 로고    scopus 로고
    • and references therein
    • (c) Khalaf, J. K.; Datta, A. J. Org. Chem. 2004, 69, 387 and references therein.
    • (2004) J. Org. Chem. , vol.69 , pp. 387
    • Khalaf, J.K.1    Datta, A.2
  • 35
    • 0033547978 scopus 로고    scopus 로고
    • and references therein. For a pioneering report
    • Ravi Kumar, J. S.; Datta, A. Tetrahedron Lett. 1999, 40, 1381 and references therein. For a pioneering report,
    • (1999) Tetrahedron Lett. , vol.40 , pp. 1381
    • Ravi Kumar, J.S.1    Datta, A.2
  • 42
    • 28044462470 scopus 로고    scopus 로고
    • note
    • One of the reviewers of the manuscript wondered why the free secondary hydroxy group (at C-3) of compound 9, generated during the conversion of 8 → 9, did not undergo further oxidation to the corresponding ketone derivative. A couple of plausible explanations could be as follows: (i) the relatively short reaction time employed for the conversion of 8 → 9 (30 min) could probably be insufficient for carrying out the two-step process of initial cleavage of the silyl protecting group to unmask the hydroxy and subsequent oxidation of this relatively hindered secondary hydroxy to the corresponding ketone. (ii) A second possibility could be an intramolecular hydrogen bond interaction between the favorably placed (and newly generated) carboxylic acid moiety at C-2 and the free hydroxy group at C-3 of compound 9, resulting in the prevention or rate retardation of the oxidation of the hydroxy group. However, additional experiments will have to be carried out to find out the exact reason for the above reaction stopping at product 9.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.