Issue 1, 2011

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

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

Supplementary files

Additions and corrections

Article information

Article type
Paper
Submitted
01 Oct 2010
Accepted
07 Dec 2010
First published
04 Feb 2011

Catal. Sci. Technol., 2011,1, 100-103

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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