title: Direct enantioselective conjugate addition of carboxylic acids with chiral lithium amides as traceless auxiliaries.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Santa Barbara, California 93106, United States.
authors.forename: Ping
authors.initials: P
authors.lastname: Lu
authors.forename: Jeffrey J
authors.initials: JJ
authors.lastname: Jackson
authors.forename: John A
authors.initials: JA
authors.lastname: Eickhoff
authors.forename: Armen
authors.initials: A
authors.lastname: Zakarian
mesh_terms: D000577:Amides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D008094:Lithium / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000577:Amides; D002264:Carboxylic Acids; D008094:Lithium