Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides: Diastereoselective and Enantioselective Substitutions
The Journal of Organic Chemistry1996Vol. 61(14), pp. 4542–4554
Citations Over TimeTop 10% of 1996 papers
Abstract
The sequence of beta-lithiation and electrophilic substitution of beta-aryl secondary amides is reported. The lithiations occur regioselectively at the beta-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of beta-lithiated amides bearing an alpha-substituent provide substituted products with high diastereoselectivity. Electrophilic substitutions of beta-lithiated N-methylamides in the presence of the chiral diamine (-)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched beta-aryl beta-substituted amides, acids, and lactones.
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