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Article Dans Une Revue Organic Letters Année : 2016

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

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Résumé

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.
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Dates et versions

hal-01403243 , version 1 (25-11-2016)

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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⟩
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