Web Release Date: June 27,
The First Directed Reduction of
-Alkoxy Ketones to anti-1,3-Diol
Monoethers: Identification of Spectator
and Director Alkoxy Groups
Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City, Utah 84112-0850
Received May 17, 2000
| Abstract: |
 |
-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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