950765-88-5Relevant academic research and scientific papers
Highly stereoselective epoxidation of α-methyl-γ-hydroxy- α,β-unsaturated esters: Rationalization and synthetic applications
Lopez, Irakusne,Rodriguez, Santiago,Izquierdo, Javier,Gonzalez, Florenci V.
, p. 6614 - 6617 (2008/02/10)
(Chemical Equation Presented) The diastereoselectivity of the nucleophilic epoxidation of γ-hydroxy-α,β-unsaturated esters having a methyl substituent at the α- or β-position was investigated. Epoxidation of the α-methyl-substituted enoate was highly stereoselective, giving rise to the syn isomer. This finding was used to perform an enantioselective synthesis of a natural product having a β-hydroxy-α-methylene- γ-butyrolactone motif. The nucleophilic epoxidation of enoates was found to be irreversible. Models to explain the observed stereoselectivities are proposed.
