ChemInform Abstract: Alkoxy-Directed Radical Reductions of Ketones Using Trichlorosilane.

✍ Scribed by Eric J. Enholm; James P. Schulte II

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199936065

✦ Synopsis

Alkoxy-Directed Radical Reductions of Ketones Using Trichlorosilane.

-A new highly diastereoselective reduction of α-hydroxy ketones with inexpensive HSiCl 3 gives predominantly anti 1,2-diols which are converted to ketals (III) and (V) for better separation of diastereomeric mixtures. Other silanes and Bu 3 SnH examined as free-radical reductants give only diketones or syn/anti products with lower diastereoselectivity. -(ENHOLM, ERIC J.;