Synthesis of chiral acetoxy lactones via the Baeyer-Villiger oxidation of cyclic aromatic acetoxy ketones


DEMİR A. G. , Aybey A.

TETRAHEDRON, cilt.64, ss.11256-11261, 2008 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 64 Konu: 49
  • Basım Tarihi: 2008
  • Doi Numarası: 10.1016/j.tet.2008.09.035
  • Dergi Adı: TETRAHEDRON
  • Sayfa Sayıları: ss.11256-11261

Özet

The alpha-acetoxylation of indanones and tetralones by using Mn(OAc)(3) followed by the enzyme catalyzed kinetic resolution of acetoxy ketones furnished both of the enantiomers of alpha-acetoxy ketones in good chemical and optical yields. The Baeyer-Villiger oxidation of alpha-acetoxy ketones with m-CPBA, CF(3)SO(3)H, and CH(2)O(2), at rt gives the corresponding lactones without racemization. The acetoxy ketone moiety migrates selectively in order to form lactones. The mild hydrolysis of lactones affords phenolic alpha-hydroxycarboxylic acid derivatives. (C) 2008 Elsevier Ltd. All rights reserved.