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 Ilepsi[CH(OH)CH2]Glu and of Ilepsi[CH(OH)CH2]Ala (in a protected form) is described.
Daniello, F., Gehanne, S., Taddei, M. (1992). A Convenient Approach To Hydroxyethylene Dipeptide Isosteres Using Allylsilane Chemistry. TETRAHEDRON LETTERS, 33(38), 5621-5624 [10.1016/S0040-4039(00)61163-2].
A Convenient Approach To Hydroxyethylene Dipeptide Isosteres Using Allylsilane Chemistry
Taddei, Maurizio
1992-01-01
Abstract
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 Ilepsi[CH(OH)CH2]Glu and of Ilepsi[CH(OH)CH2]Ala (in a protected form) is described.
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https://hdl.handle.net/11365/30962
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