title: Extending the scope of the Ferrier reaction: fragmentation-rearrangement reactions of selectively substituted 1,2-cyclopropanated glucose derivatives.
abstract: Two further variations of the Ferrier-type allylic rearrangements of 1,2-cyclopropanated glucose derivatives bearing an acetoxylated carbon at the 1'-position are described. In the first, treatment of the cyclopropanated sugar with a nucleophile (ROH, PhSH, azide) and Lewis acid (BF(3)·Et(2)O or Al(OTf)(3)), gives 2-C-vinyl glucosides in good yields and α-selectivities. Alternatively, treatment with a combination of Lewis acid and acetic acid leads to a novel fragmentation-rearrangement to form a 2,3-dehydro-2-formyl-C-glycoside.
authors.affiliation: Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa.
authors.forename: Muganza
authors.initials: M
authors.lastname: Munyololo
authors.forename: David W
authors.initials: DW
authors.lastname: Gammon
authors.forename: Ilka
authors.initials: I
authors.lastname: Mohrholz
mesh_terms: D003521:Cyclopropanes / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D003521:Cyclopropanes; C030797:cyclopropane; D005947:Glucose