Highly Stereoselective Epoxidation of α-Methyl-γ-hydroxy-α,β-unsaturated Esters: Rationalization and Synthetic Applications
2007; American Chemical Society; Volume: 72; Issue: 17 Linguagem: Inglês
10.1021/jo0709955
ISSN1520-6904
AutoresIrakusne López, Santiago Rodrı́guez, Javier Izquierdo, Florenci V. González,
Tópico(s)Cancer Treatment and Pharmacology
ResumoThe diastereoselectivity of the nucleophilic epoxidation of gamma-hydroxy-alpha,beta-unsaturated esters having a methyl substituent at the alpha- or beta-position was investigated. Epoxidation of the alpha-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 beta-hydroxy-alpha-methylene-gamma-butyrolactone motif. The nucleophilic epoxidation of enoates was found to be irreversible. Models to explain the observed stereoselectivities are proposed.
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