Catalytic Enantioselective Synthesis of Chiral Phthalides by SmI2-Mediated Reductive Cyclization of 2-Acylarylcarboxylates
- 8 April 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (17) , 5624-5625
- https://doi.org/10.1021/ja061114z
Abstract
A significant new and efficient catalytic asymmetric approach for the highly enantioselective synthesis of chiral phthalides by SmI2-induced reductive cyclization of 2-acylarylcarbonylates was developed. The combination of (4S,5R)-4,5-diphenyloxazolidin-2-one and 2,2,6,6-tetramethylpiperidine was found to be a very effective catalyst system in the reaction. This method provides a ready access to a broad range of enantiomerically enriched phthalides (up to 99% ee).Keywords
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