Chiral Phosphate in Rhodium‐Catalyzed Asymmetric [2+2+2] Cycloaddition: Ligand, Counterion, or Both? | Zendy

Barbazanges Marion | Zendy; Caytan Elsa | Zendy; Lesage Denis | Zendy; Aubert Corinne | Zendy; Fensterbank Louis | Zendy; Gandon Vincent | Zendy; Ollivier Cyril | Zendy

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Chiral Phosphate in Rhodium‐Catalyzed Asymmetric [2+2+2] Cycloaddition: Ligand, Counterion, or Both?

Author(s) -

Barbazanges Marion,

Caytan Elsa,

Lesage Denis,

Aubert Corinne,

Fensterbank Louis,

Gandon Vincent,

Ollivier Cyril

Publication year - 2016

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201601188

Subject(s) - rhodium , counterion , bimetallic strip , cycloaddition , chemistry , catalysis , ligand (biochemistry) , stereoselectivity , phosphate , medicinal chemistry , mass spectrometry , organic chemistry , ion , biochemistry , receptor , chromatography

Investigations based on NMR spectroscopy, mass spectrometry, and DFT calculations shed light on the metallic species generated in the rhodium‐catalyzed asymmetric [2+2+2] cycloaddition reaction between diynes and isocyanates with the chiral phosphate TRIP. The catalytic mixture comprising [{Rh(cod)Cl} 2 ], 1,4‐diphenylphosphinobutane (dppb), and Ag( S )‐TRIP actually gives rise to two species, both having an effect on the stereoselectivity. One is a rhodium(I) complex in which TRIP is a weakly coordinating counterion, whereas the other is a bimetallic Rh/Ag complex in which TRIP is a strongly coordinating X‐type ligand.

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