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NHC-catalyzed ester activation: Access to sterically congested spirocyclic oxindoles via reaction of α-aryl esters and unsaturated imines
L. Hao, C.W. Chuen, , Y.R. Chi
Published in
Volume: 24
Issue: 10
Pages: 1197 - 1200
Carboxylic esters can be readily obtained at low cost. Therefore, asymmetric catalytic activation of esters should provide useful strategies for organic synthesis. Here we report a N-heterocyclic carbene (NHC)-mediated reaction of α-aryl acetic esters with oxindole-derived α,β-unsaturated imines. The reaction involves the formation of NHC-bound ester enolate intermediate from an ester as a key step, and furnishes spirocyclic oxindole products. The sterically congested spirocyclic oxindole bears a newly formed six-membered δ-lactams and cannot be easily prepared using other methods. © Georg Thieme Verlag Stuttgart New York.
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