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RESEARCH PRODUCT
o-(Hydroxyalkyl)phenyl P-Chirogenic Phosphines as Functional Chiral Lewis Bases
Hiroaki SasaiYoann RousselinJerome BayardonEmmanuelle RémondShinobu TakizawaSylvain Jugésubject
Benzaldehydechemistry.chemical_compoundStereochemistryChemistryOrganic ChemistryEpimerStereoselectivityChelationLewis acids and basesPhysical and Theoretical ChemistryBoraneBiochemistryCatalysisdescription
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%.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2013-04-13 | Organic Letters |