4.8 Article

Transition-Metal-Free Cyclopropanation of 2-Aminoacrylates with N-Tosylhydrazones: A General Route to Cyclopropane α-Amino Acid with Contiguous Quaternary Carbon Centers

Journal

ORGANIC LETTERS
Volume 18, Issue 6, Pages 1470-1473

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00416

Keywords

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Funding

  1. National Natural Science Foundation of China [21472051, 21420102003]
  2. China Postdoctoral Science Foundation [2015M580717]
  3. Fundamental Research Funds for the Central Universities [2015ZY001, 2015ZM163]

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Cyclopropanation of 2-aminoacrylates with N-tosylhydrazones could proceed smoothly under transitionmetal-free conditions via a [3 + 2] cycloaddition process. This robust protocol exhibits excellent generality, delivering a wide spectrum of cyclopropane alpha-amino acid esters bearing contiguous quaternary carbon centers in high yields and diastereoselectivities. With these readily available products, the steric convergence of cyclopropane alpha-amino acids could be readily obtained.

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