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Review | Regular issue | Vol 16, No. 9, 1981, pp.1587-1601
Published online, 1st January, 1970
DOI: 10.3987/R-1981-09-1587
Acetonation of Carbohydrates under Kinetic Control by Use of 2-Alkoxypropenes

Jacques Gelas and Derek Horton*

*Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, U.S.A.


Polyols, as exemplified by the sugars and their derivatives, undergo acetonation by 2-alkoxypropenes to give cyclic acetals under kinetic control. The products generally differ from those of conventional thermodynamic acetonation and constitute chirally substituted 1,3-dioxanes, 1,3-dioxolanes, and larger heterocycles, of wide potential utility in synthesis. Free sugars react without tautomerization, and the hemiacetal hydroxyl group does not generally take part in the reaction. The stoichiometry may be controlled to give either mono- or di-acetals, and strained-ring acetals.