Zhou L,
Cheng H.-G,
*,
Li L,
Wu K,
Hou J,
Jiao C,
Deng S,
Liu Z,
Yu J.-Q,
*,
Zhou Q.
*
Wuhan University and Nankai University, Tianjin, P. R. of China; The Scripps Research
Institute, La Jolla, USA
Synthesis of Planar Chiral Ferrocenes via Enantioselective Remote C–H Activation.
Nat. Chem. 2023;
15: 815-823
DOI:
10.1038/s41557-023-01176-3
Key words
Catellani reaction - palladium catalysis - planar chiral metallocenes - remote C–H
activation
Significance
The synthesis of planar 1,3-disubstituted chiral metallocenes via palladium-catalyzed
remote C–H activation is reported. The reaction features high enantioselectivities
and good functional group tolerance. Aryl iodides as well as bromides serve as compatible
coupling partners.
Comment
An initial directed enantiodetermining C–H activation at the ortho-position, enabled by a chiral mono-N-protected natural amino acid ligand, is followed
by a C–H activation of the remote meta-position using a bridgehead-substituted norbornene mediator, akin to the Catellani
reaction.
