Enantioselective Carbocycle Formation through Intramolecular Pd-Catalyzed Allyl–Aryl Cross-Coupling | Zendy

Christopher H. Schuster | Zendy; John R. Coombs | Zendy; Zachary A. Kasun | Zendy; James P. Morken | Zendy

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Enantioselective Carbocycle Formation through Intramolecular Pd-Catalyzed Allyl–Aryl Cross-Coupling

Author(s) -

Christopher H. Schuster,

John R. Coombs,

Zachary A. Kasun,

James P. Morken

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol5019163

Subject(s) - chemistry , intramolecular force , electrophile , enantioselective synthesis , aryl , catalysis , palladium , stereoisomerism , coupling (piping) , structural isomer , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , mechanical engineering , alkyl , engineering

Aryl electrophiles containing tethered allylboronate units undergo efficient intramolecular coupling in the presence of a chiral palladium catalyst to give enantioenriched carbocyclic products. The reaction is found to be quite general, affording 5, 6, and 7-membered carbocyclic products as single regioisomers and with moderate enantioselectivities. Examination of differential coupling partners points to rapid allyl-equilibration as a key stereodefining feature.

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