RESUMO
A novel route to epoxysorbicillinol as well as dimers of sorbicillin is reported. The synthesis is-in principle-amenable to enantioselectivity. The key step is an oxidative dearomatization to produce a stable and highly malleable p-quinol intermediate, which undergoes a highly diastereoselective epoxidation.
Assuntos
Cicloexanonas/síntese química , Compostos de Epóxi/síntese química , Cicloexanonas/química , Dimerização , Compostos de Epóxi/química , Indicadores e Reagentes , Modelos Moleculares , Conformação Molecular , Estrutura Molecular , Oxirredução , Estereoisomerismo , Relação Estrutura-AtividadeRESUMO
[reaction: see text] It is surprising that chiral cations have not been used to distinguish between prochiral hydrides when converse notions, such as asymmetric addition of a hyride to a prochiral functional group or use of a chiral anion to distinguish between a pair of prochiral protons, are methods employed everyday in enantioselective synthesis. To the best of our knowledge, this Letter describes the first example of an oxidative enantioselective hydride transfer process.