Synfacts 2006(7): 0651-0651  
DOI: 10.1055/s-2006-941849
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Catalytic Pd-Mediated Approach to Enantiopure Phosphorus Ligands

Contributor(s): Victor Snieckus, Oleg M. Demchuk
M. Toffano, C. Dobrota, J.-C. Fiaud*
Université Paris Sud, Orsay, France
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Publikationsverlauf

Publikationsdatum:
22. Juni 2006 (online)

Significance

With the goal of studying the influence of the nature of the P-substituent on the 2,5-diphenylphospholane ligand properties, efficient synthetic methods for a range of enantiopure substituted P-aryl-2,5-diphenylphospholane oxides D and boranes F have been developed. The phosphinoboranes F were prepared by three different approaches from readily available corresponding enantiopure diarylphosphine oxide A, borane B or phosphinoyl chloride C in high yields and without racemization. The known phosphinoyl chloride method has some advantage over the catalytic C-P cross-coupling approaches in terms of yield but presents narrow scope. Rh-catalyzed reduction of 2,5,P-triphenylphospholane oxide affords the corresponding bulky and electron-rich tricyclohexyl derivative in excellent yield.