DBU-catalyzed Michael addition of bulky glycine imine to α,β-unsaturated isoxazoles and pyrazolamides

  1. Yu-Jun Bai,
  2. Mei-Ling Cheng,
  3. Xiao-Mu Hu,
  4. Ya-Jun Bai,
  5. Xiao-Hui Zheng,
  6. Sheng-Yong Zhang and
  7. Ping-An WangORCID Logo

Submitting author affiliation: The Fourth Military Medical University, Xi-An, China

Beilstein Arch. 2021, 202118. https://doi.org/10.3762/bxiv.2021.18.v1

Published 09 Mar 2021

  • Preprint

Abstract

A DBU-catalyzed Michael additions of several pronucleophiles with high pKa values including bulky glycine imines, α-tetra-lone, 1-methyl-2-indolone and nitroalkanes to α,β-unsaturated isoxazoles and pyrazolamides have been realized in THF with 1.0 eq. LiBr as a additive at room temperature within 3 h to provide Michael adducts in excellent yields (up to 97%) and diastereoselectivities (> 20:1).

Keywords: Michael addition; glycine imine; α,β-unsaturated isoxazole; α,β-unsaturated pyrazolamide; DBU

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Bai, Y.-J.; Cheng, M.-L.; Hu, X.-M.; Bai, Y.-J.; Zheng, X.-H.; Zhang, S.-Y.; Wang, P.-A. Beilstein Arch. 2021, 202118. doi:10.3762/bxiv.2021.18.v1

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