Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium(I) Migration | Zendy

Partridge Benjamin M. | Zendy; Callingham Michael | Zendy; Lewis William | Zendy; Lam Hon Wai | Zendy

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Arylative Intramolecular Allylation of Ketones with 1,3‐Enynes Enabled by Catalytic Alkenyl‐to‐Allyl 1,4‐Rhodium(I) Migration

Author(s) -

Partridge Benjamin M.,

Callingham Michael,

Lewis William,

Lam Hon Wai

Publication year - 2017

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201703155

Subject(s) - rhodium , intramolecular force , catalysis , chemistry , medicinal chemistry , organic chemistry

Alkenyl‐to‐allyl 1,4‐rhodium(I) migration enables the generation of nucleophilic allylrhodium(I) species by remote C−H activation. This new mode of reactivity was employed in the diastereoselective reaction of arylboron reagents with substrates containing a 1,3‐enyne tethered to a ketone, to give products containing three contiguous stereocenters. The products can be obtained in high enantioselectivities using a chiral sulfur‐alkene ligand.

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