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Volumn 47, Issue 18, 2006, Pages 3099-3102

A novel 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI)-catalyzed esterification of N-protected amino acids with nearly equimolar amounts of alcohols in the presence of Boc2O

Author keywords

[No Author keywords available]

Indexed keywords

1 TERT BUTOXY 2 TERT BUTOXYCARBONYL 1,2 DIHYDROISOQUINOLINE; ALCOHOL; AMINO ACID; ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33645842228     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.149     Document Type: Article
Times cited : (7)

References (25)
  • 3
    • 0000413286 scopus 로고
    • Barton D.H.R., and Ollis W.D. (Eds), Pergamon Press, Oxford
    • Sutherland I.O. In: Barton D.H.R., and Ollis W.D. (Eds). Comprehensive Organic Chemistry Vol. 2 (1979), Pergamon Press, Oxford 869-956
    • (1979) Comprehensive Organic Chemistry , vol.2 , pp. 869-956
    • Sutherland, I.O.1
  • 4
    • 0001674034 scopus 로고
    • Trost B.M., and Fleming I. (Eds), Pergamon Press, Oxford
    • Multtzer J. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon Press, Oxford 323
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 323
    • Multtzer, J.1
  • 14
    • 33645879925 scopus 로고    scopus 로고
    • note
    • 4) and the solvent evaporated to give the crude compound, which was purified by chromatography on a short column using a mixture of n-hexane and ethyl acetate as eluant to yield N-protected amino acid ester.
  • 15
    • 8344249465 scopus 로고    scopus 로고
    • N-Protected amino acid esters were used as chiral educts
    • N-Protected amino acid esters were used as chiral educts. Sardina F.J., and Rapoport H. Chem. Rev. 96 (1996) 1825-1872
    • (1996) Chem. Rev. , vol.96 , pp. 1825-1872
    • Sardina, F.J.1    Rapoport, H.2
  • 17
    • 33645864483 scopus 로고    scopus 로고
    • note
    • 2O gave no adduct (tert-butyl 2-tert-butoxyquinoline-1(2H)-carboxylate) similar to BBDI. Unpublished result.
  • 18
    • 33645885731 scopus 로고    scopus 로고
    • note
    • Accordingly, DMAP, quinoline, and isoquinoline would be weak as bases for tert-butoxylation of carboxylic acid.
  • 19
    • 33645848873 scopus 로고    scopus 로고
    • note
    • In fact, the enantiomeric purities of 2a, 2b and 2h were >99% ee, as determined by chiral HPLC analysis (Chiralcel OD column, 95:5 hexane/2-propanol, 1.0 mL/min) for 2a,b and (Chiralcel OJ column) for 2h.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.