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...

Full description

Saved in:
Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 359; no. 10; pp. 1678 - 1683
Main Authors Prieto, Liher, Sánchez‐Díez, Eduardo, Uria, Uxue, Reyes, Efraím, Carrillo, Luisa, Vicario, Jose L.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 17.05.2017
Wiley Subscription Services, Inc
Subjects
Activation
asymmetric catalysis
Catalysts
Chemistry
Chemistry, Applied
Chemistry, Organic
Cycloaddition
Cyclopropane
cyclopropanes
Indoles
N-heterocyclic carbenes
Organic compounds
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
ASYMMETRIC-SYNTHESIS
DIELS-ALDER REACTIONS
ENANTIOSELECTIVE SYNTHESIS
ANNULATION
ALPHA,BETA-UNSATURATED ALDEHYDES
ORGANOCATALYSIS
cyclopropanes
FORMYLCYCLOPROPANE 1,1-DIESTERS
asymmetric catalysis
3+2 CYCLOADDITION
cycloaddition
DERIVATIVES
N-heterocyclic carbenes
Online AccessGet full text

Cover

More Information
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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201700198