A flexible route to substituted hydroxy-cyclopentanones from cyclobutanones

Rama Heng (1) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

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.

Domaines: Chimie organique

Rama Heng, Samir Z. Zard. A flexible route to substituted hydroxy-cyclopentanones from cyclobutanones. Tetrahedron Letters, 2015, 56 (23), pp.3679-3682. ⟨10.1016/j.tetlet.2015.04.063⟩. ⟨hal-01186605⟩