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Diastereoselective Synthesis of Functionalized 5‐Amino‐3,4‐Dihydro‐2 H ‐Pyrrole‐2‐Carboxylic Acid Esters: One‐Pot Approach Using Commercially Available Compounds and Benign Solvents
Author(s) -
Meninno Sara,
Carratù Mario,
Overgaard Jacob,
Lattanzi Alessandra
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202005262
Subject(s) - tetrahydrofuran , chemistry , stereocenter , yield (engineering) , pyrrole , carboxylic acid , organic chemistry , diethyl carbonate , glycine , amino acid , combinatorial chemistry , solvent , catalysis , enantioselective synthesis , materials science , ethylene carbonate , biochemistry , electrode , electrolyte , metallurgy
A novel three‐step four‐transformation approach to highly functionalized 5‐amino‐3,4‐dihydro‐2 H ‐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.