Format

Send to

Choose Destination
J Am Chem Soc. 2015 Jan 21;137(2):656-9. doi: 10.1021/ja512213c. Epub 2015 Jan 8.

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

Author information

1
Department of Chemistry and Biochemistry, University of California , Santa Barbara, California 93106, United States.

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.

PMID:
25562717
PMCID:
PMC4308744
DOI:
10.1021/ja512213c
[Indexed for MEDLINE]
Free PMC Article

Supplemental Content

Full text links

Icon for American Chemical Society Icon for PubMed Central
Loading ...
Support Center