Ransborg, Lars Krogager3; Overgaard, Mette Kiilerich3; Hejmanowska, Joanna2; Barfüsser, Sebastian3; Jørgensen, Karl Anker3; Albrecht, Lukasz Karol3
1 Department of Chemistry, Science and Technology, Aarhus University2 Lodz Technical University3 Department of Chemistry, Science and Technology, Aarhus University
An organocatalytic one-pot cascade leading to the stereoselective formation of novel bridged benzoxazocines is presented. The developed methodology is based on the first example of a γ-selective-Mannich-initiated cascade reaction and allows for direct annulation of the bridged benzoxazocines by incorporation of various α,β-unsaturated aldehydes, electron-rich anilines, and electron-deficient salicylaldehydes. The synthetic applicability of the products is demonstrated by relevant transformations.
Organic Letters, 2014, Vol 16, Issue 16, p. 4182-4185