A Convenient Approach to Hydroxyethylene Dipeptide Isosteres using Allylsilane Chemistry

Article abstract of DOI:10.1016/S0040-4039(00)61163-2

2-Chloromethyl-3-trimethylsilyl-1-propene reacts with N-Boc amino aldehydes in the presence of BF3*OEt2 to give selectively the corresponding (S)-homoallylic alcohols.These compounds can be easily transformed into hydroxyethylene dipeptide isosteres through elaboration of the allylic chloride part of the molecule.The preparation of IleψGlu and of IleψAla (in a protected form) is described.