4.6 Article

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

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 14, Pages 4573-4577

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202005262

Keywords

amidines; diastereoselectivity; green solvents; metal-free; one-pot reaction

Funding

  1. MUR
  2. University of Salerno
  3. PON RI

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A novel three-step four-transformation approach was developed for the synthesis of highly functionalized 5-amino-3,4-dihydro-2H-pyrrole-2-carboxylic acid esters, delivering amidines bearing three contiguous stereocenters. The entire sequence was carried out using benign solvents and metal-free conditions, demonstrating the synthetic utility of the products at scale-up.
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.

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