Fe3+-Catalyzed transacetalization of 2-alkoxytetrahydrofurans with alcohols

Tetrahedron Letters

Volumn 49, Issue 1, 2008, Pages 53-56

  Yamanaka, Daisetsu ^a   Matsunaga, Sei ^a   Kawamura, Yasufumi ^a   Hosokawa, Takahiro ^a  

^a KOCHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

Ferric perchlorate; Tetrahydrofuran derivatives; Transacetalization

Indexed keywords

ALCOHOL; ANTINEOPLASTIC AGENT; FERRIC ION; MAGNESIUM DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; ZINC DERIVATIVE;

ACETALIZATION; ARTICLE; CATALYST; CHEMICAL REACTION;

EID: 36549086425     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.018     Document Type: Article

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23. 3+ was allowed to coordinate at either the pyranyl or furanyl acetal moiety, and further optimization was made by 3-21G/B3LYP. As a result, only the former case led to the optimization of the stabilized conformer.
24. At the early stage of the reaction, the formation of a small amount of 2a was observed by NMR.
25. 3 (10 mol %) in THF for 10 min gave 1b in ∼90% yield.
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