Bond cleavage, fragment modification and reassembly in enantioselective three-component reactions

Dan Zhang, Jun Zhou, Fei Xia, Zhenghui Kang and Wenhao Hu ()
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Dan Zhang: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University
Jun Zhou: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University
Fei Xia: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University
Zhenghui Kang: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University
Wenhao Hu: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University

Nature Communications, 2015, vol. 6, issue 1, 1-8

Abstract: Abstract Chemical bond cleavage and reconstruction are common processes in traditional rearrangement reactions. In contrast, the process that involves bond cleavage, fragment modification and then reconstruction of the modified fragment provides an efficient way to build structurally diversified molecules. Here, we report a palladium(II)/chiral phosphoric acid catalysed three-component reaction of aryldiazoacetates, enamines and imines to afford α-amino-δ-oxo pentanoic acid derivatives in good yields with excellent diastereoselectivities and high enantioselectivities. The stereoselective reaction went through a unique process that involves cleavage of a C–N bond, modification of the resulting amino fragment and selective reassembly of the modified fragment. This innovative multi-component process represents a highly efficient way to build structurally diversified polyfunctional molecules in an atom and step economic fashion. A keto-iminium is proposed as a key intermediate and a chiral palladium/phosphate complex is proposed as an active catalyst.

Date: 2015
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DOI: 10.1038/ncomms6801

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