Open AccessA New Entry to Azomethine Ylides from Allylic Amines and Glyoxals: Shifting the Reliance on Amino Ester Precursors
Author(s) -
Natalie K. Machamer,
Xiaoxi Liu,
Stephen P. Waters
Publication year - 2014
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol5022614
Subject(s) - chemistry , allylic rearrangement , azomethine ylide , pyrrolidine , glyoxal , cycloaddition , amine gas treating , conjugated system , aryl , condensation , organic chemistry , catalysis , 1,3 dipolar cycloaddition , polymer , alkyl , physics , thermodynamics
The first examples of azomethine ylides derived from allylic amine and glyoxal precursors are reported. The condensation of primary allylic and α-aryl amines with glyoxylates or α-aryl glyoxals affords conjugated azomethine ylides that undergo facile [3 + 2] cycloaddition, providing 5-alkenyl pyrrolidine cycloadducts that cannot be accessed through the classical use of amino esters as ylide precursors.
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