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Issue 1, 2011
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Novel N,O-Cu(OAc)2 complex catalysed diastereo- and enantioselective 1,4-addition of glycine derivatives to alkylidene malonates

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Abstract

Newly developed chiral N,O-Cu(OAc)2 complexes were found to catalyse the diastereo- and enantioselective 1,4-addition of glycine derivatives to alkylidene malonates to afford 3-aryl glutamic acids derivatives in good yields (82–98%) and high stereoselectivities (up to 83% for anti and 90% for syn adducts, respectively). High optical purity anti adducts (up to 99% ee) can be obtained after simple recrystallisation, and their conversion to free 3-aryl glutamic acids was demonstrated by a representative example, chlorpheg, via a one pot process in 72% yield.

Graphical abstract: Novel N,O-Cu(OAc)2 complex catalysed diastereo- and enantioselective 1,4-addition of glycine derivatives to alkylidene malonates

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Publication details

The article was received on 01 Oct 2010, accepted on 07 Dec 2010 and first published on 04 Feb 2011


Article type: Paper
DOI: 10.1039/C0CY00001A
Citation: Catal. Sci. Technol., 2011,1, 100-103
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    Novel N,O-Cu(OAc)2 complex catalysed diastereo- and enantioselective 1,4-addition of glycine derivatives to alkylidene malonates

    M. Wang, Y. Shi, J. Luo, W. Du, X. Shi, J. S. Fossey and W. Deng, Catal. Sci. Technol., 2011, 1, 100
    DOI: 10.1039/C0CY00001A

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