Synthetic Applications of the β-Lithiation of β-Aryl Secondary Amides: Diastereoselective and Enantioselective Substitutions
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (14) , 4542-4554
- https://doi.org/10.1021/jo952223r
Abstract
The sequence of β-lithiation and electrophilic substitution of β-aryl secondary amides is reported. The lithiations occur regioselectively at the β-position, and the resulting lithiated intermediates can be reacted with a wide range of electrophiles to give substituted products. Reactions of β-lithiated amides bearing an α-substituent provide substituted products with high diastereoselectivity. Electrophilic substitutions of β-lithiated N-methylamides in the presence of the chiral diamine (−)-sparteine provide highly enantioenriched products. The methodology is used to synthesize enantioenriched β-aryl β-substituted amides, acids, and lactones.Keywords
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