title: o-(Hydroxyalkyl)phenyl P-chirogenic phosphines as functional chiral Lewis bases.
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%.
authors.affiliation: Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB-StéréochIM), UMR CNRS 6302, 9 Avenue Alain Savary, BP 47870, 21078 Dijon cedex, France.
authors.forename: Emmanuelle
authors.initials: E
authors.lastname: Rémond
authors.forename: Jérôme
authors.initials: J
authors.lastname: Bayardon
authors.forename: Shinobu
authors.initials: S
authors.lastname: Takizawa
authors.forename: Yoann
authors.initials: Y
authors.lastname: Rousselin
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Sasai
authors.forename: Sylvain
authors.initials: S
authors.lastname: Jugé