Journal
CHEMICAL SCIENCE
Volume 3, Issue 1, Pages 121-125Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1sc00441g
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Funding
- NSF [CHE-1049571]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1049571] Funding Source: National Science Foundation
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Using N-sulfinyl urea catalysis, a method has been developed for the asymmetric synthesis of biologically important gamma-amino acids with a high level of efficiency, practicality and unprecedented control of multiple stereocenters. This method is based upon the highly enantio-and diastereoselective addition of cyclohexyl Meldrum's acid as an easily deprotectable monocarboxylic acid equivalent. The addition to both beta-substituted and alpha,beta-disubstituted nitroalkenes using N-sulfinyl urea organocatalyst 8 is described. The utility of this new method toward drug production is demonstrated by the mole scale preparation of a key precursor to the commercial drug Lyrica using catalyst 8 at only 0.2 mol% loading. Moreover, alpha,beta-disubstituted nitroalkene addition products were efficiently converted to g-amino acid derivatives without epimerization of either stereocenter.
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