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Updated: Feb 13, 2026

Fabricating Reactive Surfaces with Brush-like and Crosslinked Films of Azlactone-Functionalized Block Co-Polymers
Published on: June 30, 2018
A Brønsted base-promoted diastereoselective dimerization of azlactones
Danielle L J Pinheiro1, Gabriel M F Batista1, Pedro P de Castro1
1Chemistry Department, Federal University of Juiz de Fora, Cidade Universitária, São Pedro, Juiz de Fora, MG, CEP 36036-900, Brazil.
Abstract:
A novel Brønsted base system for the diastereoselective dimerization of azlactones using trichloroacetate salts and acetonitrile has been developed. Desired products were obtained in good yields (60-93%) and with up to >19:1 dr after one hour of reaction. Additionally, the relative stereochemistry of the major dimer was assigned as being trans, by X-ray crystallographic analysis. The kinetic reaction profile was determined by using 1H NMR reaction monitoring and revealed a second order overall kinetic profile. Furthermore, by employing this methodology, a diastereoselective total synthesis of a functionalized analogue of streptopyrrolidine was accomplished in 65% overall yield.
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