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Volumn 50, Issue 12, 2009, Pages 1298-1300

Asymmetric cycloetherification based on a chiral auxiliary for 4-acyloxy-1-butene substrates during oxidation with iodosylbenzene via a 1,3-dioxan-2-yl cation

Author keywords

Chiral auxiliary; Hypervalent iodine; Iodosylbenzene; Neighboring group participation; Tetrahydrofuran

Indexed keywords

1,3 DIOXAN 2 YL; 4 ACYLOXY 1 BUTENE; BUTANE; DIOXANE DERIVATIVE; IODOSOBENZENE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 59349089320     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.01.012     Document Type: Article
Times cited : (43)

References (40)
  • 20
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    • In: Wirth T. (Ed). Hypervalent Iodine Chemistry (2003), Springer, Berlin
    • (2003) Hypervalent Iodine Chemistry
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    • 0031027260 scopus 로고    scopus 로고
    • For recent reviews, see:
    • For recent reviews, see:. Varvoglis A. Tetrahedron 53 (1997) 1179-1255
    • (1997) Tetrahedron , vol.53 , pp. 1179-1255
    • Varvoglis, A.1
  • 31
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    • For a related paper, see:
    • For a related paper, see:. Fujita M., Lee H.J., and Okuyama T. Org. Lett. 8 (2006) 1399-1401
    • (2006) Org. Lett. , vol.8 , pp. 1399-1401
    • Fujita, M.1    Lee, H.J.2    Okuyama, T.3
  • 32
    • 59349111396 scopus 로고    scopus 로고
    • note
    • An authentic sample of S-2 was prepared by esterification of (S)-3-hydroxytetrahydrofuran (TCI).
  • 33
    • 59349114632 scopus 로고    scopus 로고
    • note
    • If epimerization at the α-position of the carboxylate of 1a-c (2a-c) took place during the reaction, diastereomeric ratio should be affected. No experimental examination for the epimerization was carried out. The poor diastereomeric ratio obtained is not suitable for asymmetric synthesis whether it takes place or not.
  • 34
    • 77956770660 scopus 로고
    • Gold V., and Bethell D. (Eds), Academic Press, London
    • Kirby A.J. In: Gold V., and Bethell D. (Eds). Advances in Physical Organic Chemistry Vol. 17 (1980), Academic Press, London 183-278
    • (1980) Advances in Physical Organic Chemistry , vol.17 , pp. 183-278
    • Kirby, A.J.1
  • 38
    • 59349121315 scopus 로고    scopus 로고
    • note
    • 5b was detected by HPLC equipped with a chiral column (Daicel chiralpak AD).
  • 39
    • 59349120432 scopus 로고    scopus 로고
    • note
    • 5c
  • 40
    • 59349111880 scopus 로고    scopus 로고
    • note
    • Enantiomeric purity of the hydroxytetrahydrofuran was determined by HPLC analysis (Daicel chiralpak AD column) of cis-3-benzoyloxy-2-(triethylsilyl)tetrahydrofuran derived from the hydroxytetrahydrofuran.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.