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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.

SUBMITTER: Lu P

PROVIDER: S-EPMC4308744 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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Direct enantioselective conjugate addition of carboxylic acids with chiral lithium amides as traceless auxiliaries.

Lu Ping P Jackson Jeffrey J JJ Eickhoff John A JA Zakarian Armen A

Journal of the American Chemical Society 20150108 2

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 ...[more]

PMID: 25562717

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