posted on 2016-01-05, 12:06authored byPing Lu, Jeffrey J. Jackson, John A. Eickhoff, Armen Zakarian
Michael
addition is a premier synthetic method for carbon–carbon
and carbon–heteroatom bond formation. Using chiral dilithium
amides as traceless auxiliaries, we report the direct enantioselective
Michael addition of carboxylic acids. A free carboxyl group in the
product provides versatility for further functionalization, and the
chiral reagent can be readily recovered by extraction with aqueous
acid. The method has been applied in the enantioselective total synthesis
of the purported structure of pulveraven B.