Development of simple, amino acid-based catalysts for enantioselective silylation of alcohols

ORGN 310

Yu Zhao,, Jason Rodrigo, Amir H. Hoveyda, and Marc L. Snapper. Department of Chemistry, Boston College, 2609 Beacon Street, Chestnut Hill, MA 02467
While significant advances in catalytic asymmetric acylations and phosphorylations of alcohols have been achieved in recent years, the resulting functionalities are not popular protecting groups in organic synthesis. A catalytic asymmetric silylation of alcohols, on the other hand, which would provide chiral silyl ethers directly, culd address this shortcoming. In this regard, we will describe the first, highly selective desymmetrization of meso-diols through a direct catalytic asymmetric silylation. This transformation uses common silyl chlorides and affords chiral silyl ethers in up to 96% ee and 96% yields. The catalyst is a simple, amino acid-based organic molecule prepared in three steps from commercially available materials. An extension of this strategy utilizing functionalized silyl chlorides will also be discussed.