NHC-Catalyzed Ester Activation: Access to Sterically Congested Spirocyclic Oxindoles via Reaction of α-Aryl Esters and Unsaturated Imines

Autor:	Yonggui Robin Chi, Chan Wei Chuen, Rakesh Ganguly, Lin Hao
Přispěvatelé:	School of Physical and Mathematical Sciences
Rok vydání:	2013
Předmět:	Steric effects chemistry.chemical_compound chemistry Aryl Science::Chemistry::Organic chemistry [DRNTU] Organic Chemistry Organic synthesis Oxindole Combinatorial chemistry Carbene Catalysis
Zdroj:	Synlett. 24:1197-1200
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-0033-1338945
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ccde262af900915c840d9922e49aa260 https://doi.org/10.1055/s-0033-1338945 Zobrazit plný text záznamu