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Split‐ Ugi Reaction with Chiral Compounds: Synthesis of Piperazine‐ and Bispidine‐Based Peptidomimetics
Author(s) -
Stucchi Mattia,
Lesma Giordano
Publication year - 2016
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201500505
Subject(s) - chemistry , peptidomimetic , piperazine , ugi reaction , combinatorial chemistry , stereochemistry , organic chemistry , peptide , biochemistry , isocyanide
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.