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Development of Enantioselective Palladium‐Catalyzed Alkene Carboalkoxylation Reactions for the Synthesis of Tetrahydrofurans
Author(s) -
Hopkins Brett A.,
Garlets Zachary J.,
Wolfe John P.
Publication year - 2015
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.201506884
Subject(s) - stereocenter , palladium , tetrahydrofuran , enantioselective synthesis , aryl , alkene , chemistry , catalysis , ligand (biochemistry) , yield (engineering) , combinatorial chemistry , organic chemistry , solvent , materials science , alkyl , biochemistry , receptor , metallurgy
The Pd‐catalyzed coupling of γ‐hydroxyalkenes with aryl bromides affords enantiomerically enriched 2‐(arylmethyl)tetrahydrofuran derivatives in good yield and up to 96:4 e.r. This transformation was achieved through the development of a new TADDOL/2‐arylcyclohexanol‐derived chiral phosphite ligand. The transformations are effective with an array of different aryl bromides, and can be used for the preparation of products bearing quaternary stereocenters.