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N-Heterocyclic Carbene Catalyzed Homoenolate-Addition Reaction of Enals and Nitroalkenes: Asymmetric Synthesis of 5-Carbon-Synthon δ-Nitroesters

Authors

  • Dr. Biswajit Maji,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
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  • Li Ji,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
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  • Siming Wang,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
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  • Seenuvasan Vedachalam,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
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  • Dr. Rakesh Ganguly,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
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  • Dr. Xue-Wei Liu

    Corresponding author
    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
    • Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
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  • We gratefully acknowledge the support of Nanyang Technological University (NTU; RG 50/08) and the Ministry of Health Singapore (MOH; NMRC/H1N1R/001/2009) for financial support.

Abstract

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Synthesizing synthons: The highly enantioselective title reaction is described. It employs catalytic amounts of N-heterocyclic carbene precursors and transforms a broad range of nitroalkenes, such as nitrodienes, nitroenynes, and nitrostyrenes, through reaction with a broad range of enals, into δ-nitroesters via homoenolate intermediates (see scheme).

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