Synthesis of phosphole-2,5-dicarboxylic acids via a [1,5]-shift of carbon dioxide around the phosphole nucleus

Mohand Melaimi; Louis Ricard; François Mathey; Pascal Le Floch

doi:10.1021/ol0102895

Synthesis of phosphole-2,5-dicarboxylic acids via a [1,5]-shift of carbon dioxide around the phosphole nucleus

Org Lett. 2002 Apr 18;4(8):1245-7. doi: 10.1021/ol0102895.

Authors

Mohand Melaimi¹, Louis Ricard, François Mathey, Pascal Le Floch

Affiliation

¹ Laboratoire "Hétéroéléments et Coordination", UMR CNRS 7653, Ecole Polytechnique, 91128 Palaiseau Cedex, France.

PMID: 11950333
DOI: 10.1021/ol0102895

Abstract

A new methodology for the synthesis of 1-P-functionalized phosphole-2,5-dicarboxylic acids is described. The carboxylic group is introduced through a two-step sequence which involves a preliminary attack of the phospholide unit onto CO(2) followed by a [1,5]-shift reaction of the CO(2)Li group around the phosphole nucleus. This approach was extended to the preparation of a new type of bidentate ligands. [reaction: see text]