Assessing the Activity of Lewis Bases Organocatalysts in Halonium-Induced Carbocyclization Reactions

Charlotte Grandclaudon; Mirko Ruamps; Raphaël Duboc; Véronique Michelet; Patrick Y. Toullec

doi:10.1055/s-0036-1591982

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(09): 1181-1186
DOI: 10.1055/s-0036-1591982

letter

Assessing the Activity of Lewis Bases Organocatalysts in Halonium-Induced Carbocyclization Reactions

Charlotte Grandclaudon

^aInstitut de Recherche de Chimie Paris PSL Research University, Chimie ParisTech-CNRS, 11 Rue P. et M. Curie, 75005 Paris, France

,

Mirko Ruamps

^aInstitut de Recherche de Chimie Paris PSL Research University, Chimie ParisTech-CNRS, 11 Rue P. et M. Curie, 75005 Paris, France

,

Raphaël Duboc

^aInstitut de Recherche de Chimie Paris PSL Research University, Chimie ParisTech-CNRS, 11 Rue P. et M. Curie, 75005 Paris, France

,

Véronique Michelet

^aInstitut de Recherche de Chimie Paris PSL Research University, Chimie ParisTech-CNRS, 11 Rue P. et M. Curie, 75005 Paris, France

^bInstitut de Chimie de Nice, Université Nice Sophia Antipolis UMR CNRS, 7272 Parc Valrose, 06108 Nice, France

,

Patrick Y. Toullec *

^aInstitut de Recherche de Chimie Paris PSL Research University, Chimie ParisTech-CNRS, 11 Rue P. et M. Curie, 75005 Paris, France

^cInstitute of Molecular Sciences University of Bordeaux, 351, Cours de la Libération, 33405 Talence, France eMail: patrick.toullec@u-bordeaux.fr

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Abstract

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Abstract

Lewis bases were evaluated as catalysts for halocarbocyclization reactions of alkynylstyrenes and a cinnamylaniline derivative. Phosphines and phosphorus chalcogenides exhibited high activity for the conversion of alkynylstyrenes in the presence of N-halosuccinimides with up to a 30-fold increase of the initial reaction rate with respect to the background reaction. Phosphorus sulfides and selenides showed the best catalytic activity for the iodocarbocyclization of a cinnamylaniline derivative in the presence of diiodohydantoin. An asymmetric variant of the iodocarbocyclization reaction of an alkynylstyrene using a chiral phosphorus selenide resulted in a modest enantioselectivity.

Key words

organocatalysis - Lewis base - halogenation - carbocyclization - enynes

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Referenzen

References and Notes

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Zusatzmaterial

Supporting Information