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Volumn 50, Issue 33, 2009, Pages 4700-4702

A facile synthesis of 4-methylene-1,3-oxazolidines from γ-hydroxybutynoate and N-tosylimines

Author keywords

Activated propargylic alcohol; Methyleneoxazolidine; Organocatalysis; Phosphine catalyzed

Indexed keywords

ALCOHOL; GAMMA HYDROXYBUTYNOATE; METHYLENEOXAZOLIDINE; N TOSYLIMINE; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 67649342030     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.009     Document Type: Article
Times cited : (7)

References (42)
  • 15
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    • 53849119129 scopus 로고    scopus 로고
    • For a review on the synthesis of methylenetetrahydrofurans by [3+2] annulations see:
    • For a review on the synthesis of methylenetetrahydrofurans by [3+2] annulations see:. Yamazaki S. Chem. Eur. J. 14 (2008) 6026-6036
    • (2008) Chem. Eur. J. , vol.14 , pp. 6026-6036
    • Yamazaki, S.1
  • 33
    • 67649357397 scopus 로고    scopus 로고
    • note
    • 2 (2 mL) under argon atmosphere. The resulting mixture was stirred at room temperature for 24 h and the solvents were removed. The crude product was purified by TLC on silica gel plates (heptane/ethyl acetate, 7/3 mixture) to give the pure Z- and E-isomers of the final oxazolidine 3a. No defined by-products have been isolated from these reactions.
  • 34
    • 67649308927 scopus 로고    scopus 로고
    • note
    • 3) δ 21.8, 52.1, 68.2, 94.1, 106.6, 126.7, 128.1, 128.8, 129.3, 130.0, 135.1, 136.8, 144.1, 145.1, 166.0 ppm.
  • 39
    • 33745941049 scopus 로고    scopus 로고
    • For uses of t-Bu-Binepine as chiral organocatalyst, see:
    • For uses of t-Bu-Binepine as chiral organocatalyst, see:. Wilson J.E., and Fu G.C. Angew. Chem., Int. Ed. 45 (2006) 1426-1429
    • (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 1426-1429
    • Wilson, J.E.1    Fu, G.C.2
  • 42
    • 67649374150 scopus 로고    scopus 로고
    • note
    • Racemization of the stereogenic carbon of 3a due to the basic reaction conditions cannot be ruled out.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.