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

Author:
Zhu, Dong-Xing, Chen, Wen-Wen, Xu, Ming-Hua
Source:
Tetrahedron 2016 v.72 pp. 2637-2642
ISSN:
0040-4020
Subject:
acids, carbon, chemical reactions, enantiomers, ketones, ligands, olefin
Abstract:
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).
Agid:
5292065