Synthesis 2014; 46(10): 1334-1338
DOI: 10.1055/s-0033-1338612
special topic
© Georg Thieme Verlag Stuttgart · New York

Synergistic Iron-and-Amine Catalysis in Carbocyclizations

Chandrasekaran Praveen
Institut de Recherche de Chimie Paris, CNRS – Chimie ParisTech, 11 rue Pierre et Marie Curie, 75005 Paris, France   Email: veronique.michelet@chimie-paristech.fr   Email: virginie.vidal@chimie-paristech.fr
,
Sabine Levêque
Institut de Recherche de Chimie Paris, CNRS – Chimie ParisTech, 11 rue Pierre et Marie Curie, 75005 Paris, France   Email: veronique.michelet@chimie-paristech.fr   Email: virginie.vidal@chimie-paristech.fr
,
Maxime R. Vitale
Institut de Recherche de Chimie Paris, CNRS – Chimie ParisTech, 11 rue Pierre et Marie Curie, 75005 Paris, France   Email: veronique.michelet@chimie-paristech.fr   Email: virginie.vidal@chimie-paristech.fr
,
Véronique Michelet*
Institut de Recherche de Chimie Paris, CNRS – Chimie ParisTech, 11 rue Pierre et Marie Curie, 75005 Paris, France   Email: veronique.michelet@chimie-paristech.fr   Email: virginie.vidal@chimie-paristech.fr
,
Virginie Ratovelomanana-Vidal*
Institut de Recherche de Chimie Paris, CNRS – Chimie ParisTech, 11 rue Pierre et Marie Curie, 75005 Paris, France   Email: veronique.michelet@chimie-paristech.fr   Email: virginie.vidal@chimie-paristech.fr
› Author Affiliations
Further Information

Publication History

Received: 08 January 2014

Accepted after revision: 25 February 2014

Publication Date:
19 March 2014 (eFirst)

Dedicated to Professor Max Malacria on the occasion of his 65th birthday

Abstract

The fruitful merger of iron catalysis to amine catalysis was successfully applied in the direct intramolecular addition of aldehydes to non-activated alkynes. Accordingly, the carbocyclizations of a range of formyl-alkynes afforded the corresponding cyclopentanes in good to excellent yields. Experimental evidence tends to support a synergistic enamine/π-activation reaction mechanism.

 
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