A Convenient Approach to Hydroxyethylene Dipeptide Isosteres using Allylsilane Chemistry

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

Source and publish data:

Tetrahedron Letters p. 5621 - 5624 (1992)

Update date:2022-08-03

Topics:

Authors:

D'Aniello, Fabiana

Gehanne, Sylvie

Taddei, Maurizio

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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.

Full text of DOI:10.1016/S0040-4039(00)61163-2

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