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Issue 1, 2012
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Enantio- and diastereoselective addition of cyclohexyl Meldrum's acid to β- and α,β-disubstituted nitroalkenesvia N-sulfinyl urea catalysis

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Abstract

Using N-sulfinyl urea catalysis, a method has been developed for the asymmetric synthesis of biologically important γ-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 β-substituted and α,β-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, α,β-disubstituted nitroalkene addition products were efficiently converted to γ-amino acid derivatives without epimerization of either stereocenter.

Graphical abstract: Enantio- and diastereoselective addition of cyclohexyl Meldrum's acid to β- and α,β-disubstituted nitroalkenesvia N-sulfinyl urea catalysis

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Publication details

The article was received on 08 Jul 2011, accepted on 29 Jul 2011 and first published on 25 Aug 2011


Article type: Edge Article
DOI: 10.1039/C1SC00441G
Citation: Chem. Sci., 2012,3, 121-125
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    Enantio- and diastereoselective addition of cyclohexyl Meldrum's acid to β- and α,β-disubstituted nitroalkenesvia N-sulfinyl urea catalysis

    K. L. Kimmel, J. D. Weaver and J. A. Ellman, Chem. Sci., 2012, 3, 121
    DOI: 10.1039/C1SC00441G

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