Integrated One-Pot Synthesis of 1,3-Oxazinan-2-ones from Isocyanoacetates and Phenyl Vinyl Selenones

Authors

  • Thomas Buyck Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, CH-1015 Lausanne, Switzerland
  • Qian Wang Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, CH-1015 Lausanne, Switzerland
  • Jieping Zhu Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, CH-1015 Lausanne, Switzerland. jieping.zhu@epfl.ch

DOI:

https://doi.org/10.2533/chimia.2015.199

Keywords:

Cinchona, Domino reaction, Isocyanoacetates, Oxidative mcr, Selenones

Abstract

Brønsted base (Et3N or DBU) catalyzed Michael addition of α-substituted α-isocyanoacetates to phenyl vinyl selenones followed by a Brønsted acid (PTSA) catalyzed domino oxidative cyclization afforded 1,3-oxazinan-2-ones in good to excellent yields. Enantio-enriched 1,3-oxazinan-2-ones were accessible using a Cinchona alkaloid-derived bifunctional catalyst for the first step. In this integrated one-pot process, the phenyl selenonyl group acted consecutively as an activator, a leaving group and a latent oxidant.

CHIMIA Vol. 69 No. 4 (2015): Laureates: Junior Prizes, SCS Fall Meeting 2014

Downloads

Published

2015-04-29

Issue

Vol. 69 No. 4 (2015): Laureates: Junior Prizes, SCS Fall Meeting 2014

Section

Scientific Articles

License

Copyright (c) 2015 Swiss Chemical Society

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

How to Cite

[1]
Chimia 2015, 69, 199, DOI: 10.2533/chimia.2015.199.