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Diastereoselective Synthesis of Functionalized 5-Amino-3,4-Dihydro-2H-Pyrrole-2-Carboxylic Acid Esters: One-Pot Approach Using Commercially Available Compounds and Benign Solvents

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  • Sara Meninno, University of Salerno
  • ,
  • Mario Carratù, University of Salerno
  • ,
  • Jacob Overgaard
  • Alessandra Lattanzi, University of Salerno

A novel three-step four-transformation approach to highly functionalized 5-amino-3,4-dihydro-2H-pyrrole-2-carboxylic acid esters, starting from commercially available phenylsulfonylacetonitrile, aldehydes, and N-(diphenylmethylene)glycine tert-butyl ester, was developed. The one-pot strategy delivered this class of amidines bearing, for the first time, three contiguous stereocenters, in good to high yield and diastereoselectivity. The entire sequence was carried out using diethyl carbonate and 2-methyl tetrahydrofuran as benign solvents, operating under metal-free conditions. The process could be conveniently scaled-up, and the synthetic utility of the products was demonstrated.

OriginalsprogEngelsk
TidsskriftChemistry - A European Journal
Vol/bind27
Nummer14
Sider (fra-til)4573-4577
Antal sider5
ISSN0947-6539
DOI
StatusUdgivet - mar. 2021

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