Split-Ugi Reaction with Chiral Compounds: Synthesis of Piperazine- and Bispidine-Based Peptidomimetics

July 28, 2017

Title

Split-Ugi Reaction with Chiral Compounds: Synthesis of Piperazine- and Bispidine-Based Peptidomimetics

Author

Mattia Stucchi, Giordano Lesma

Year

2016

Journal

Helvetica Chimica Acta

Abstract

A simple, one-step, stereoconservative synthesis of diamine-based peptidomimetics is described, by split-Ugi multicomponent reaction, involving chiral N-protected amino acids and α-substituted isocyanoacetate. In particular, piperazine and bispidine (3,7-diazabicyclo[3.3.1]nonane) are exploited as diamine components, bispidine being the first example of a sterically demanding bicyclic system employed in a split-Ugi reaction.

Instrument

J-715

Keywords

Circular dichroism, Absolute configuration