4.5 Article

Sequential Ir-Catalyzed Allylation/2-aza-Cope Rearrangement Strategy for the Construction of Chiral Homoallylic Amines†

Journal

CHINESE JOURNAL OF CHEMISTRY
Volume 38, Issue 8, Pages 807-811

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202000065

Keywords

Asymmetric catalysis; Homoallylic amine; Arylidene aminomalonates; Allylation; 2-aza-Cope rearrangement

Funding

  1. National Natural Science Foundation of China [21525207, 21772147]
  2. Natural Science Foundation of Jiangsu Province [SKB2019041078]
  3. Wuhan Morning Light Plan of Youth Science and Technology [2017050304010307]
  4. Postdoctoral Innovative Talent Support Program of China [BX20190253]

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The Summary of main observation and conclusion Sequential Ir-catalyzed asymmetric allylation/2-aza-Cope rearrangement of arylidene aminomalonates with allylic carbonates was successfully developed, and a variety of enantioenriched homoallylic amine derivatives were obtained in high yields with good chirality transfer and excellent E/Z-geometry control (up to 99% yield, 96% ee). Compared with previous dual catalytic system established for this transformation, the current mono metal catalytic system provides a simpler and more practical protocol employing the readily available starting materials.

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