Designing P-Chirogenic 1,2-Diphosphinobenzenes at Both P-Centers Using P(III)-Phosphinites

Jérôme Bayardon (1) , Yoann Rousselin (1) , Sylvain Jugé (1)

1 ICMUB - Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon]

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.

Mots clés: catalyzed asymmetric hydrogenation; highly enantioselective hydrogenation; functionalized alkenes; phospholane ligands; phosphine-ligands; carbon-monoxide; hydroformylation; ketones; organocatalysis; derivatives

Domaines: Chimie; Chimie organique

Jérôme Bayardon, Yoann Rousselin, Sylvain Jugé. Designing P-Chirogenic 1,2-Diphosphinobenzenes at Both P-Centers Using P(III)-Phosphinites. Organic Letters, 2016, 18 (12), pp.2930 - 2933. ⟨10.1021/acs.orglett.6b01275⟩. ⟨hal-01403243⟩