A flexible route to substituted hydroxy-cyclopentanones from cyclobutanones

作者：Heng Rama; Zard Samir Z^*

来源：Tetrahedron Letters, 2015, 56(23): 3679-3682.

DOI：10.1016/j.tetlet.2015.04.063

• Cyclobutanones
• Cyclopentanones
• Radical addition
• Xanthates
• Ring expansion

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.

• 出版日期2015-6-3