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

Ming Wang; Yu-Hua Shi; Jun-Fei Luo; Wenting Du; Xiao-Xin Shi; John S. Fossey; Wei-Ping Deng

doi:10.1039/C0CY00001A

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Catalysis Science & Technology

Issue 1, 2011

A multidisciplinary journal focussing on all fundamental science and technological aspects of catalysis

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

Ming Wang,^a Yu-Hua Shi,^a Jun-Fei Luo,^a Wenting Du,^a Xiao-Xin Shi,^a John S. Fossey^a^b and Wei-Ping Deng*^a

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School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
E-mail: weiping_deng@ecust.edu.cn ;
Tel: +86 (21) 64252431

School of Chemistry, University of Birmingham, Edgbaston, Birmingham, UK

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

DOI: 10.1039/C0CY00001A
Received 01 Oct 2010, Accepted 07 Dec 2010
First published online 04 Feb 2011

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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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Ming Wang
Yu-Hua Shi
Jun-Fei Luo
Wenting Du
Xiao-Xin Shi
John S. Fossey
Wei-Ping Deng

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