A flexible route to substituted hydroxy-cyclopentanones from cyclobutanones

Abstract : Acetonyl radicals derived from TBS-protected 1-(alpha-xanthylacetyl)-1-cyclobutanes readily undergo addition to unactivated alkenes. Deprotection of the resulting adducts with Et4NF/THF and exposure to silica gel cause ring expansion to give substituted hydroxycyclopentanones. Products of addition to ally! cyanide also underwent beta-elimination of the xanthate when treated with Et4NF/THF. (C) 2015 Elsevier Ltd. All rights reserved.