Abstract
2-Chloromethyl-3-trimethylsilyl-1-propene reacts with N-Boc amino aldehydes in the presence of BF 3 OEt 2 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 Ileψ[CH(OH)CH 2]Glu and of Ileψ[CH(OH)CH 2]Ala (in a protected form) is described.
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