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Silver‐Catalyzed Diastereoselective Synthesis of Spirocyclic Pyrrolidine‐Lactones by 1,3‐Dipolar Cycloaddition
Author(s) -
GarcíaMingüens Eduardo,
Caletková Oľga,
Berkeš Dušan,
Nájera Carmen,
Sansano José M.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000915
Subject(s) - chemistry , pyrrolidine , cycloaddition , imine , electrophile , enantioselective synthesis , catalysis , 1,3 dipolar cycloaddition , electrophilic amination , combinatorial chemistry , organic chemistry , stereochemistry , computational chemistry , amination
The preparation of two enantiomerically enriched amino lactones as chiral starting substrates for asymmetric 1,3‐dipolar cycloadditions is described. They act as precursors of the chiral imino lactones, which form in situ the corresponding azomethine ylides. They react with electrophilic alkenes under silver catalysis to afford spirolactone‐pyrrolidines products. The sequential method consisting in one‐pot imine formation → cycloaddition is optimized and compared with the multicomponent process. The scope of the reaction is studied as well as the stereochemical outcomes and the mechanistic details using DFT calculations and X‐ray diffraction analysis.