Rhodium-catalyzed asymmetric intramolecular addition of arylboronic acids to ketones: catalytic enantioselective access to 3-hydroxy-2,3-dihydrobenzofurans bearing a tetrasubstituted carbon stereocenter

A highly enantioselective rhodium-catalyzed intramolecular addition of arylboronic acids to unactivated ketones has been developed. By employing a simple, chiral sulfur-based branched olefin as the ligand, the reaction occurs efficiently under mild conditions. A wide range of chiral 3-hydroxy-2,3-di...

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Bibliographic Details
Published in:Tetrahedron 2016-05, Vol.72 (21), p.2637-2642
Main Authors: Zhu, Dong-Xing, Chen, Wen-Wen, Xu, Ming-Hua
Format: Article
Language:English
Subjects:
Asymmetric catalysis
Asymmetry
Bearing
Carbon
Catalysis
Dihydrobenzofuran
Intramolecular addition
Ketones
Ligands
Olefins
Rhodium
Sulfur-olefin ligand
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Summary:A highly enantioselective rhodium-catalyzed intramolecular addition of arylboronic acids to unactivated ketones has been developed. By employing a simple, chiral sulfur-based branched olefin as the ligand, the reaction occurs efficiently under mild conditions. A wide range of chiral 3-hydroxy-2,3-dihydrobenzofurans bearing a tetrasubstituted stereocenter at C-3 position can be obtained in high yields (up to 98%) with excellent enantiomeric excesses (up to 98% ee). [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.04.030