American Chemical Society
ja512213c_si_001.pdf (1.92 MB)

Direct Enantioselective Conjugate Addition of Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries

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journal contribution
posted on 2016-01-05, 12:06 authored by Ping 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.