Catalytic Generation of Donor-Acceptor Cyclopropanes under N-Heterocyclic Carbene Activation and their Stereoselective Reaction with Alkylideneoxindoles

Formylcyclopropanes undergo activation in the presence of an N-heterocyclic carbene catalyst generating a donor-acceptor cyclopropane intermediate with the ability to undergo ring-opening followed by formal [4+2] cycloaddition with alkylideneoxindoles. This enables the direct enantio- and diastereos...

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Bibliographic Details
Authors: Prieto Aretxabaleta, Liher, Sánchez Díez, Eduardo, Uria Pujana, Uxue, Reyes Martín, Efraim, Carrillo Fernández, María Luisa, Vicario Hernando, José Luis
Format: article
Publication Date:2017
Country:España
Institution:Universidad del País Vasco
Repository:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/64341
Online Access:http://hdl.handle.net/10810/64341
Access Level:Open access
Keyword:asymmetric catalysis
cycloaddition
cyclopropanes
N-heterocyclic carbenes
Description
Summary:Formylcyclopropanes undergo activation in the presence of an N-heterocyclic carbene catalyst generating a donor-acceptor cyclopropane intermediate with the ability to undergo ring-opening followed by formal [4+2] cycloaddition with alkylideneoxindoles. This enables the direct enantio- and diastereoselective synthesis of tetrahydropyrano[ 2,3-b]indoles through the use of a chiral NHC catalyst. Keywords: asymmetric

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