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Synlett 1991; 1991(10): 702-704
DOI: 10.1055/s-1991-34763
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Chelation-Controlled Regio- and Stereoselective C-Allylation of Glycosides and Related Cyclic Hemiacetals

Olivier R. Martin* , S. Prahlada Rao, Te-Fang Yang, Frank Fotia
  • *Department of Chemistry, SUNY-University Center, P.O. Box 6000, Binghamton, New York 13902-6000, USA
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13. März 2002 (online)

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Reaction of xylofuranoside 4, glucopyranoside 13, and the related hemiacetals 10, 16, and 17 with allyltrimethylsilane and titanium(IV) chloride resulted in allylation at C-1 to give acyclic products with a high degree of stereoselectivity. Chelation of the Lewis acid at O-4/O-5 or O-5/O-6 in the glycosides is thought to be responsible for the unusual substitution of their endocyclic C-O bond under these conditions.