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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.
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Submitted on : Tuesday, August 25, 2015 - 12:43:14 PM
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Rama Heng, Samir Z. Zard. A flexible route to substituted hydroxy-cyclopentanones from cyclobutanones. Tetrahedron Letters, Elsevier, 2015, 56 (23), pp.3679-3682. ⟨10.1016/j.tetlet.2015.04.063⟩. ⟨hal-01186605⟩



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