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Volumn 54, Issue 30, 1998, Pages 8827-8840

The use of phosphinamide N-protecting groups in the diastereoselective reduction of ketones

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; KETONE; PEPSTATIN; PHOSPHINAMIDE; PROTEINASE; UNCLASSIFIED DRUG;

EID: 0032560725     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00474-8     Document Type: Article
Times cited : (12)

References (36)
  • 1
    • 0001172518 scopus 로고
    • ed. Barrett, A. J.; Salvesen, G. Elsevier, New York
    • 1. Review: Rich, D. H. "Proteinase Inhibitors", ed. Barrett, A. J.; Salvesen, G. Elsevier, New York, 1986, p.179. Recent synthesis featuring carbonyl reduction: Nishi, T.; Kitamura, M.; Ohkuma, T.; Noyori, R. Tetrahedron Lett., 1988, 29, 6327.
    • (1986) Proteinase Inhibitors , pp. 179
    • Rich, D.H.1
  • 2
    • 45549111026 scopus 로고
    • Recent synthesis featuring carbonyl reduction
    • 1. Review: Rich, D. H. "Proteinase Inhibitors", ed. Barrett, A. J.; Salvesen, G. Elsevier, New York, 1986, p.179. Recent synthesis featuring carbonyl reduction: Nishi, T.; Kitamura, M.; Ohkuma, T.; Noyori, R. Tetrahedron Lett., 1988, 29, 6327.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 6327
    • Nishi, T.1    Kitamura, M.2    Ohkuma, T.3    Noyori, R.4
  • 25
    • 0010470549 scopus 로고    scopus 로고
    • note
    • 8. During an attempt to prepare 8a via the N-diphenylphosphinyl derivative of S-methylalanamide we found that racemisation occured when the ester was coupled to (S,S)-(+)-psuedoephedrine using n-butyllithium as a base. Although this rendered this approach unsuitable for the required application, its conversion to 9a provided a convenient method for the preparation of enantiomeric standards for the Mosher ester analysis.
  • 27
    • 0010430505 scopus 로고    scopus 로고
    • note
    • 12 in 70% yield.
  • 28
    • 0010508225 scopus 로고    scopus 로고
    • note
    • 7b In our hands 8c was formed in 71% yield from the corresponding acid and 8b was formed in 31% overall yield from the t-Boc protected valine (4 processes in two pots, as described in the text).
  • 30
    • 0010508035 scopus 로고    scopus 로고
    • note
    • 4c
  • 31
    • 0010430986 scopus 로고    scopus 로고
    • note
    • 14. Reduction of 15 with sodium borohydride gave a 2:1 mixture of diastereoisomeric products 16 (90% yield), thereby conveniently providing a sample which confirmed the selectivity of the borane reduction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.