Evolution of a ‘privileged’ P-alkene ligand: added planar chirality beats BINOL axial chirality in catalytic asymmetric C–C bond formation

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

doi:10.1039/D3CC04972H

Evolution of a ‘privileged’ P-alkene ligand: added planar chirality beats BINOL axial chirality in catalytic asymmetric C–C bond formation†‡

Luisa Leinauer,^a Giorgio Parla,^a Julian Messelbeger,^a Alberto Herrera,*^a Frank W. Heinemann,^a Jens Langer,

^a Ilya Chuchelkin,

^b Alexander Grasruck,^a Sibylle Frieß,^a Ahmed Chelouan,^c Konstantin Gavrilov

^b and Romano Dorta

*^a

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* Corresponding authors

^a Department of Chemistry and Pahrmacy, Chair of Inorganic and General Chemistry, Friedrich Alexander Universität Erlangen–Nürnberg, Egerlandstraße 1, 91058 Erlangen, Germany
E-mail: romano.dorta@fau.de

^b Department of Chemistry, Ryazan State University Named after S. Yesenin, 46 Svoboda Street, 390000 Ryazan, Russian Federation

^c Department of Chemistry, Abdelmalek Essaadi University, B.P. 2121, 39, Hannech II, 93002 Tétouan, Morocco

Abstract

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.

Chemical Communications

Evolution of a ‘privileged’ P-alkene ligand: added planar chirality beats BINOL axial chirality in catalytic asymmetric C–C bond formation†‡

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Evolution of a ‘privileged’ P-alkene ligand: added planar chirality beats BINOL axial chirality in catalytic asymmetric C–C bond formation

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