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Unprecedented Synthesis of 4‐Ylidene (3 S )‐3‐hydroxy‐1‐aryl (alkyl)‐pyrrolidine‐2,5‐diones Based on 1,3‐Dipolar Cycloaddition of a Sugar‐derived Nitrone to N ‐Substituted Maleimides
Author(s) -
Ghannay Siwar,
Alminderej Fahad,
Msaddek Moncef,
Praly JeanPierre,
Aouadi Kaïss
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900931
Subject(s) - nitrone , cycloaddition , pyrrolidine , chemistry , stereocenter , aryl , alkyl , maleimide , medicinal chemistry , bond cleavage , organic chemistry , catalysis , enantioselective synthesis
1,3‐Dipolar cycloaddition of a sugar‐based nitrone to differently N ‐substituted maleimides afforded mixtures of isoxazolidine‐based cycloadducts. The obtained predominant cycloadducts displayed three new contiguous stereogenic centers placing the protons in syn and anti ‐relationship, respectively at the fused bond, and for H 5 and H 6 . This was explained by an endo approach of the maleimide derivatives to the Si ‐face of the nitrone reacting in its Z ‐form. The mCPBA‐mediated oxidative cleavage N−O bond of the isoxazolidine occurred almost quantitatively to afford unprecedented sugar nitrones. Their pyrolysis under thermal or microwave activation led to new 4‐ylidene (3 S )‐3‐hydroxy‐1‐aryl (alkyl)‐pyrrolidine‐2,5‐diones.