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

Alkene planar chirality is introduced in the 'privileged' P-alkene phosphoramidite ligand 1 . The resulting diastereomeric ligands (p R,R )- 5 and (p S,R )- 5 form optically pure complexes of Rh( i ) and Pd( ii ), which catalyze conjugate additions of boron C-nucleophiles to enones and all...

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Published in:Chemical communications (Cambridge, England) England), 2023-12, Vol.59 (97), p.14451-14454
Main Authors: Leinauer, Luisa, Parla, Giorgio, Messelbeger, Julian, Herrera, Alberto, Heinemann, Frank W, Langer, Jens, Chuchelkin, Ilya, Grasruck, Alexander, Frieß, Sibylle, Chelouan, Ahmed, Gavrilov, Konstantin, Dorta, Romano
Format: Article
Language:English
Subjects:
Alkenes
Alkylation
Chirality
Covalent bonds
Ligands
Nucleophiles
Rhodium
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Summary:Alkene planar chirality is introduced in the 'privileged' P-alkene phosphoramidite ligand 1 . The resulting diastereomeric ligands (p R,R )- 5 and (p S,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. Planar chirality is introduced in a 'privileged' P-alkene phosphoramidite ligand and shown to overwhelm the chirality of the BINOL auxiliary.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc04972h