ChemInform Abstract: The SHi Reaction at Silicon — A New Entry into Cyclic Alkoxysilanes.

✍ Scribed by Armido Studer; Hanno Steen

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199924175

✦ Synopsis

Intramolecular homolytic substitution reactions at silicon to generate cyclic five-membered alkoxysilanes need a trimethylstannyl substituent at the silicon as leaving group, e.g. (IV), or additional trimethylsilyl groups, e.g. (V), to get high yields. Since a tin radical is liberated in this new mild method, the process is considered as unimolecular chain-transfer reaction. With this method excellent 1,2-diastereoselectivity may be obtained, e.g. (IX) and (XII). These reaction products can easily be converted to the corresponding diol derivatives, e.g. (X) and (XIV) by Tamao-Fleming oxidation. The diols are a synthetically important class of compounds. -(STUDER, ARMIDO; STEEN, HANNO;