Application of Isocyanides Derived from α-Amino Acids as Substrates for the Ugi Reaction

Stanislaw Berlozecki, Wiktor Szymanski, Ryszard Ostaszewski*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

16 Citaten (Scopus)

Samenvatting

A systematic study on the influence of Lewis acid, solvent, and temperature on the stereochemical course of the Ugi reaction was performed to find conditions in which the isocyanides derived from enantiopure alpha-amino acids do not racemize. After a series of experiments, dichloromethane was used as a solvent and BF(3)center dot OEt(2) as a Lewis acid catalyst. This combination allowed us to obtain a product in a model reaction with 99% diastereoisomeric ratio (dr), with the structure motif of a group of cathepsin K inhibitors.

Originele taal-2English
Pagina's (van-tot)2714-2721
Aantal pagina's8
TijdschriftSynthetic Communications
Volume38
Nummer van het tijdschrift16
DOI's
StatusPublished - 2008
Extern gepubliceerdJa

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