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Updated: May 12, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
Published on: November 22, 2016
o-(Hydroxyalkyl)phenyl P-chirogenic phosphines as functional chiral Lewis bases
Emmanuelle Rémond1, Jérôme Bayardon, Shinobu Takizawa
1Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB-StéréochIM), UMR CNRS 6302, 9 Avenue Alain Savary, BP 47870, 21078 Dijon cedex, France.
Abstract:
The stereoselective synthesis of P-chirogenic phosphines bearing an o-hydroxyalkyl chelating arm is described. The synthesis is based either on the hydroxyalkylation of P-chirogenic o-bromophenylphosphines (borane) or on their carbonatation and then reduction. The hydroxyalkylation with benzaldehyde or pivalaldehyde affords a mixture of epimers which are isolated by chromatography and characterized by their X-ray structures. Preliminary assays of free P-chirogenic o-(hydroxyalkyl)phenyl phosphines, as new functional Lewis bases in catalyzed asymmetric aza-MBH reaction, lead to β-aminoester derivatives with ee values up to 74%.
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