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Title: NHC-catalyzed ester activation : access to sterically congested spirocyclic oxindoles via reaction of α-aryl esters and unsaturated imines
Authors: Hao, Lin
Chuen, Chan Wei
Ganguly, Rakesh
Chi, Robin Yonggui
Keywords: DRNTU::Science::Chemistry::Organic chemistry
Issue Date: 2013
Source: Hao, L., Chuen, C. W., Ganguly, R., & Chi, Y. R. (2013). NHC-Catalyzed Ester Activation: Access to Sterically Congested Spirocyclic Oxindoles via Reaction of α-Aryl Esters and Unsaturated Imines. Synlett, 24(10), 1197–1200.
Series/Report no.: Synlett
Abstract: 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.
ISSN: 0936-5214
DOI: 10.1055/s-0033-1338945
Rights: © 2013 Georg Thieme Verlag Stuttgart · New York.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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