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Stereoselective Lewis Acid Mediated (3+2) Cycloadditions of N ‐H‐ and N ‐Sulfonylaziridines with Heterocumulenes
Author(s) -
Craig Robert A.,
O'Connor Nicholas R.,
Goldberg Alexander F. G.,
Stoltz Brian M.
Publication year - 2014
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.201303699
Subject(s) - stereoselectivity , cycloaddition , chemistry , sulfonyl , derivatization , context (archaeology) , lewis acids and bases , aryl , alkyl , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , high performance liquid chromatography , paleontology , biology
Alkyl and aryl isothiocyanates and carbodiimides are effective substrates in (3+2) cycloadditions with N ‐sulfonyl‐2‐substituted aziridines and 2‐phenylaziridine for the synthesis of iminothiazolidines and iminoimidazolidines. Additionally, the stereoselective (3+2) cycloaddition of N ‐H‐ and N ‐sulfonylaziridines with isothiocyanates can be accomplished, allowing for the synthesis of highly enantioenriched iminothiazolidines. Evidence for an intimate ion‐pair mechanism is presented herein in the context of these chemo‐, regio‐, and diastereoselective transformations. The demonstrated ability to remove the sulfonyl group from the heterocyclic products displays the utility of these compounds for further derivatization and application.