Synthesis
DOI: 10.1055/s-0036-1590901
paper
© Georg Thieme Verlag Stuttgart · New York

Two-Step Synthesis of α,β-Unsaturated γ-Amino Acid Esters via N-Heterocyclic Carbene Catalyzed [4+2] Cycloaddition of Enals and Nitroso Compounds

Qiang Liu, Xiang-Yu Chen, Sun Li, Fabrizio Vetica, Gerhard Raabe, Dieter Enders*
  • Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
Further Information

Publication History

Received: 02 August 2017

Accepted: 11 August 2017

Publication Date:
07 September 2017 (eFirst)

Abstract

An efficient strategy for the synthesis of various of α,β-unsaturated γ-amino acid esters has been established employing N-heterocyclic carbene catalyzed [4+2] cycloadditions of β-methyl enals and aromatic nitroso compounds to afford 1,2-oxazin-6-ones in good yields. A subsequent acid-catalyzed esterification under ring opening yields the γ-amino enoates in good yields.

Supporting Information