1062505-08-1Relevant articles and documents
Sequential C-Si bond formations from diphenylsilane: Application to silanediol peptide isostere precursors
Nielsen, Lone,Skrydstrup, Troels
supporting information; experimental part, p. 13145 - 13151 (2009/03/12)
The report of silanediol peptide isosteres as highly active inhibitors of proteolytic enzymes has triggered an increased interest for these compounds, thereby necessitating a general and direct synthetic access to this unusual class of protease inhibitors. In this paper, we report on thetwo-step assembly of the carbon-silicon backbone of a silane-containing dipeptide fragment. The synthetic scheme is comprised of an alkene hydr osilylation step with the simple precursor, diphenylsilane, using eithera radical initiator or RhCl(PPh 3)3, Wilkinson's catalyst, for the creation of a hydridosilane and the first new carbon-s ilicon bond. The next step is the reduction of this hydridosilane with lithium metal providing a silyl lithium reagent, which undergoes a highlydiastereoselective addition to an optically active tert-butanesulfinimi ne, thus generating the second C-Si bond. This method allows sequential functionalization of the two hydrides in diphenylsilane by chemoselective discrimination.
