GaCl3-catalyzed insertion of isocyanides into a C-O bond in cyclic ketals and acetals

Organic Letters

Volumn 7, Issue 17, 2005, Pages 3697-3699

  Yoshioka, Sachiko ^a   Oshita, Masayuki ^a   Tobisu, Mamoru ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

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Indexed keywords

EID: 24044476549     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0513138     Document Type: Article

References (27)

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18. For the importance of catalyst detachment from the product in Lewis acid catalysis: Morrison, D. J.; Piers, W. E. Org. Lett. 2003, 5, 2857.
19. For reactions of acetals or ketals with isocyanide that lead to different types of product than that shown in eq 1: (a) Mukaiyama, T.; Watanabe, K.; Shiono, M. Chem. Lett. 1974, 1457.
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22. Unidentified byproducts other than 3 were also observed by GC analysis of the crude reaction mixture. On isolation of the products, ca. 38% of the isocyanie was recovered.
23. For similar discussions on substituent effects, see ref 7.
24. These compounds are potentially useful for organic synthesis since hydrolysis of the imino moiety should afford 1,4-dioxane-2-one derivative. See ref 9b.
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