6533b852fe1ef96bd12aabc6
RESEARCH PRODUCT
Designing P-Chirogenic 1,2-Diphosphinobenzenes at Both P-Centers Using P(III)-Phosphinites
Yoann RousselinJérôme BayardonSylvain Jugésubject
phosphine-ligandsDIPAMPketonesStereochemistryBoranesDABCOBorane010402 general chemistry[ CHIM ] Chemical Sciences01 natural sciencesBiochemistryArynecatalyzed asymmetric hydrogenationchemistry.chemical_compoundfunctionalized alkenes[ CHIM.ORGA ] Chemical Sciences/Organic chemistry[CHIM]Chemical SciencesorganocatalysisPhysical and Theoretical Chemistryhydroformylation010405 organic chemistryChemistry[CHIM.ORGA]Chemical Sciences/Organic chemistryOrganic Chemistrycarbon-monoxide0104 chemical scienceshighly enantioselective hydrogenationOrganocatalysisderivativesStereoselectivityChirality (chemistry)phospholane ligandsdescription
International audience; A new enantiodivergent synthesis of P-chirogenic 1,2-diphosphinobenzenes (DP*B) bearing the chirality on one or both phosphorus centers is reported using aryne chemistry. The principle is based on successive reactions of 1,2-dibromobenzene with sec-phosphide boranes, then DABCO to remove the borane, and finally with chlorophosphines or P(III)-chirogenic phosphinites. The efficiency of this synthesis was demonstrated by the stereoselective preparation of (S,S)-1,2-bis(o-anisylphenylphosphino)benzene. A comparison of DIPAMP and homochiral DP*B ligands in asymmetric Rh- or Pd-catalyzed reactions was reported.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-05-31 |