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Volumn 53, Issue 46, 1997, Pages 15671-15680

Preparation of enantiopure 4-oxygenated pipecolic acid derivatives

Author keywords

[No Author keywords available]

Indexed keywords

PIPECOLIC ACID DERIVATIVE;

EID: 0030735857     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10059-X     Document Type: Article
Times cited : (25)

References (37)
  • 28
  • 29
    • 0343704695 scopus 로고    scopus 로고
    • Personal communication
    • Plante, R. Personal communication.
    • Plante, R.1
  • 30
    • 0343269040 scopus 로고    scopus 로고
    • note
    • Ultimately the absolute stereochemistry was proven when an X-ray structure of palinavir dihydrochloride was obtained with material which was identical in all aspects with the one described here, see ref. 9b.
  • 32
    • 0342399472 scopus 로고
    • and references cited therein
    • ß-Methyl L-aspartate hydrochloride was purchased from Omega Chemicals, Québec city or was readily prepared from thionyl chloride and L-aspartic acid in methanol. See: Khosla, M. C.; Smeby, R. R. and Bumpus, F. M. Ind. J. Chem. 1967, 5 (6), 279 and references cited therein.
    • (1967) Ind. J. Chem. , vol.5 , Issue.6 , pp. 279
    • Khosla, M.C.1    Smeby, R.R.2    Bumpus, F.M.3
  • 33
    • 0343704693 scopus 로고    scopus 로고
    • note
    • Three equivalents of sodium methoxide were required for optimal results in this transformation. Use of fewer equivalents of sodium methoxide or use of other bases i.e. : NaH, KH, KO-t-Bu, LiHMDS, NaHMDS, or KHMDS all resulted in lower yields.
  • 35
    • 0343269036 scopus 로고    scopus 로고
    • note
    • (R)-(-)-1-indanol and (S)-(+)-1-indanol were purchased from Aldrich Chemical Co. The (R)-(-) enantiomer was found to have an ee of 99.8% and the (S)-(+) enantiomer was found to have an ee of 99.7%. These ee's were obtained by HPLC analysis using a Daicel chiral pak AS 4.6 × 250 mm column, eluent: 10% EtOH/hexane isocratic at 0.5 mL/min., PDA detector at 205 nm.
  • 37
    • 0342399471 scopus 로고    scopus 로고
    • note
    • R for the (R)-indanyl ester : 13.5 min (detection limit <0.5%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.