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Research

ENANTIOSELCTIVE SILYLATION OF ALCOHOLS   

Researchers - Yu Zhao, Jason Rodrigo, Zhen You, Aurpon Mitra

Silyl groups are one of the most (if not the most) widely used protecting groups for alcohols.  Chiral catalysts can greatly facilitate the access to optically enriched organic molecules.  A catalyst that promotes enantioselective silylation of alcohols, however, has not been reported.  We have developed the first effective chiral silylation catalyst that initiates highly enantioselective desymmetrization of a wide range of meso-diols.  The catalytic asymmetric alcohol silylations require common commercially available silyl chlorides and afford chiral silyl ethers in up to 96% ee and 96% yield.  The catalyst is a simple (MW = 308 g/mole), amino acid-based organic molecule prepared in three straightforward steps from commercially available materials.  Extensions of the scope of the asymmetric silylation are currently under investigation.

Silylation

John Traverse

James Porter

Andy Leyhane

 

 

   
 
     
 
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