Letters in Organic Chemistry

Gwilherm Evano
Free University of Brussels
Brussels
Belgium

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Iodoalkene-Based Approach Towards Carboxamides of Biological Importance: Aminocarbonylation of 2-Iodobornene and 3-Iodo-2- quinuclidene

Author(s): Laszlo Horvath, Andrea Petz, Laszlo Kollar.

Abstract:

The palladium-catalysed aminocarbonylation of 2-iodobornene and 3-iodo-2-quinuclidene, possessing iodo alkene functionality, resulted in the high-yielding synthesis of the corresponding carboxamide derivatives. The substrates were synthesised from camphor and 3-quinuclidone, respectively, via their hydrazones. The chemoselective homogeneous carbonylation reaction of synthetic value was carried out under mild reaction conditions. While the carbonylation of the 2- iodobornene was found to be a facile reaction with yields of synthetic interest, its isomer, 1-iodocamphene, formed in Wagner-Meervein rearrangement, remained intact under the same reaction conditions.

Keywords: Iodoalkenes, aminocarbonylation, carbon monoxide, palladium, camphor, quinuclidene

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Article Details

VOLUME: 7
ISSUE: 1
Year: 2010
Page: [54 - 60]
Pages: 7
DOI: 10.2174/157017810790534048