An Improved Catalyst for the Asymmetric Arylation of Ketone Enolates
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- 26 January 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (7) , 1261-1268
- https://doi.org/10.1021/ja011122+
Abstract
A new catalyst system for the enantioselective α-arylation of ketones is reported. This catalyst, prepared from Pd2(dba)3 and a bulky dialkylphosphino-binaphthyl ligand, is able to effect the asymmetric arylation of ketone enolates with aryl bromides utilizing NaOtBu as base. These new catalysts enjoy much higher reactivity than previous systems; arylation reactions could be effected at room temperature with only 2 mol % of the Pd catalyst. The coupling of α-alkyl-α‘-protected cyclopentanones proceeded in high yield, and the resulting quaternary stereogenic center was installed in up to 94% ee.Keywords
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