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

Literature Information

Publication Date 2011-02-04
DOI 10.1039/C0CY00001A
Impact Factor 6.119
Authors

Ming Wang, Yu-Hua Shi, Jun-Fei Luo, Wenting Du, Xiao-Xin Shi, Wei-Ping Deng


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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.

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Catalysis Science & Technology

Catalysis Science & Technology
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