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.

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Published

2015-04-29