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Volumn , Issue 2, 1996, Pages 223-229

Enantioselective syntheses of (R)- and (S)-hexahydropyridazine-3-carboxylic acid derivatives

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; PYRIDAZINE DERIVATIVE;

EID: 0029924489     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4192     Document Type: Article
Times cited : (29)

References (58)
  • 12
    • 9044249343 scopus 로고
    • Ph. D. Thesis, Utah State University, Logan, Utah/USA
    • Nelson, W. R. Ph. D. Thesis, Utah State University, Logan, Utah/USA, 1987.
    • (1987)
    • Nelson, W.R.1
  • 32
    • 9044242283 scopus 로고    scopus 로고
    • Merck & Co, Inc. U.S.-Patent 5026703
    • (a) Bock, M. G.; Freidinger, R. M.; DiPardo, R. M.; Merck & Co, Inc. U.S.-Patent 5026703; Chem. Abstr. 1991, 115, 256660n.
    • Bock, M.G.1    Freidinger, R.M.2    DiPardo, R.M.3
  • 33
    • 9044252732 scopus 로고
    • (a) Bock, M. G.; Freidinger, R. M.; DiPardo, R. M.; Merck & Co, Inc. U.S.-Patent 5026703; Chem. Abstr. 1991, 115, 256660n.
    • (1991) Chem. Abstr. , vol.115
  • 35
    • 85023479515 scopus 로고
    • (b) Goetz, M. A.; Schwartz, C. D.; Koupal, L. R.; Liesch, J. M.; Hansens, O. D.; Freidinger, R.; Anderson, P. S.; Pettibone, D. J., Woodruff, B. H.; Merck & Co, Inc. Eur. Patent 0327744 A1; Chem. Abstr. 1990, 112, 215199p.
    • (1990) Chem. Abstr. , vol.112 , pp. 215199
  • 53
    • 85088330684 scopus 로고    scopus 로고
    • note
    • 4 had to be used to accelerate the reaction because in the alkaline aqueous solution the lactone was opened to the carboxylate which does not react further.
  • 54
    • 9044243045 scopus 로고    scopus 로고
    • note
    • There are several publications (for example refs 34, 39 and 40) using 2-hydroxy-5-(hydroxymethyl)tetrahydrofuran in organic syntheses, all of them using disiamylborane or DIBAL for reduction of the lactone to the lactol. We tried also to stop the reduction at the stage of the lactol using DIBAL in THF. We got only about 30% yield as further reduction to the diol could not be avoided.
  • 55
    • 9044235599 scopus 로고    scopus 로고
    • If tetrabutylammonium fluoride was used acetyl migration to the δ-position took place
    • If tetrabutylammonium fluoride was used acetyl migration to the δ-position took place.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.