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Volumn , Issue 1, 2003, Pages 83-86

Highly efficient 4-O-alkylations of tetronic acids involving oxyphosphonium intermediates

Author keywords

Alkylations; Mitsunobu reaction; Phosphonium ions; Regioselectivity; Tetronic acids

Indexed keywords

(5 OXO 2,5 DIHYDROFURAN 3 YLOXY)PHOSPHONIUM TRIFLUOROMETHANESULFONATE DERIVATIVE; 5H FURAN 2 ONE DERIVATIVE; ALCOHOL; FURAN DERIVATIVE; OXYPHOSPHONIUM DERIVATIVE; PHOSPHONIUM DERIVATIVE; SULFONIC ACID DERIVATIVE; TETRONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037244322     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (13)

References (23)
  • 5
    • 0034072953 scopus 로고    scopus 로고
    • For leading references, see: (a) Schobert, R.; Siegfried, S. Synlett 2000, 686. (b) Sato, T.; Koji, Y.; Otera, J. Synlett 1995, 843. (c) Hoffmann, H. M.; Schmidt, B.; Wolff, S. Tetrahedron 1989, 45, 6113; and references cited therein.
    • (2000) Synlett , pp. 686
    • Schobert, R.1    Siegfried, S.2
  • 6
    • 0142152760 scopus 로고
    • For leading references, see: (a) Schobert, R.; Siegfried, S. Synlett 2000, 686. (b) Sato, T.; Koji, Y.; Otera, J. Synlett 1995, 843. (c) Hoffmann, H. M.; Schmidt, B.; Wolff, S. Tetrahedron 1989, 45, 6113; and references cited therein.
    • (1995) Synlett , pp. 843
    • Sato, T.1    Koji, Y.2    Otera, J.3
  • 7
    • 45249130139 scopus 로고
    • and references cited therein
    • For leading references, see: (a) Schobert, R.; Siegfried, S. Synlett 2000, 686. (b) Sato, T.; Koji, Y.; Otera, J. Synlett 1995, 843. (c) Hoffmann, H. M.; Schmidt, B.; Wolff, S. Tetrahedron 1989, 45, 6113; and references cited therein.
    • (1989) Tetrahedron , vol.45 , pp. 6113
    • Hoffmann, H.M.1    Schmidt, B.2    Wolff, S.3
  • 11
    • 0000870705 scopus 로고    scopus 로고
    • Analogous side reactions are well known for Mitsunobu esterifications with hindered alcohols. For a detailed mechanistic discussion, see: Hughes, D. L.; Reamer, R. A. J. Org. Chem. 1996, 61, 2967.
    • (1996) J. Org. Chem. , vol.61 , pp. 2967
    • Hughes, D.L.1    Reamer, R.A.2
  • 14
    • 0012729064 scopus 로고    scopus 로고
    • note
    • 2NEt (209 μL, 1.25 mmol). Then the reaction mixture was allowed to warm to r.t. and stirred for 20 h, before it was concentrated under reduced pressure. The crude product was purified by flash chromatography.
  • 15
    • 0012696410 scopus 로고    scopus 로고
    • note
    • Abstract
  • 17
    • 0024259859 scopus 로고
    • 2, Δ) according to Spahn led to the corresponding 2-octyl esters. The ratio of diastereomers was determined by GC from the crude reaction product: Spahn, H. Arch. Pharm. (Weinheim, Ger.) 1988, 321, 847.
    • (1988) Arch. Pharm. (Weinheim, Ger.) , vol.321 , pp. 847
    • Spahn, H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.