The first directed reduction of beta-alkoxy ketones to anti-1,3-diol monoethers: identification of spectator and director alkoxy groups.
Org Lett
; 2(15): 2307-9, 2000 Jul 27.
Article
em En
| MEDLINE
| ID: mdl-10930270
A new reduction procedure for the stereoselective reduction of certain beta-alkoxy ketones is described. The method relies upon electron-transfer reduction using samarium diiodide in THF with MeOH as an additive. Reduction is facile for a number of alkoxy groups that can complex samarium effectively but is not observed with TBS or benzyl protecting groups. Experiments with deuterated methanol show that the stereoselectivity arises from protonation of a samarium carbanion intermediate.
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Base de dados:
MEDLINE
Assunto principal:
Éteres
/
Cetonas
Tipo de estudo:
Diagnostic_studies
Idioma:
En
Ano de publicação:
2000
Tipo de documento:
Article