Highly Stereoselective Synthesis of Substituted Prolyl Peptides Using a Combination of Biocatalytic Desymmetrization and Multicomponent Reactions

Anass Znabet, Eelco Ruijter, Frans J. J. de Kanter, Valentin Köhler, Madeleine Helliwell, Nicholas J. Turner, Romano V. A. Orrù

Angewandte Chemie International Edition · 2010 · 119 citations · 29 references

Concepts

Abstract

Time and pep-tide wait for no man: Optically pure 3,4-disubstituted 1-pyrrolines, generated from the corresponding meso-pyrrolidines by biocatalytic desymmetrization (MAO-N=monoamine oxidase N), react with carboxylic acids and isocyanides in a highly diastereoselective Ugi-type multicomponent reaction to give substituted prolyl peptides of high pharmaceutical relevance.

References

29