Evolution of a ‘privileged’ P-alkene ligand: added planar chirality beats BINOL axial chirality in catalytic asymmetric C–C bond formation‡
Literature Information
Luisa Leinauer, Giorgio Parla, Julian Messelbeger, Alberto Herrera, Frank W. Heinemann, Jens Langer, Ilya Chuchelkin, Alexander Grasruck, Sibylle Frieß, Ahmed Chelouan, Konstantin Gavrilov, Romano Dorta
Alkene planar chirality is introduced in the ‘privileged’ P-alkene phosphoramidite ligand 1. The resulting diastereomeric ligands (pR,R)-5 and (pS,R)-5 form optically pure complexes of Rh(I) and Pd(II), which catalyze conjugate additions of boron C-nucleophiles to enones and allylic alkylations, respectively. In the Rh-catalyzed reaction, the planar chirality of the alkene exerts absolute enantiocontrol over the potent BINOL auxiliary.
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Chemical Communications

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