4.5 Article

Assembly of Trifluoromethylated Morpholines through Cascade Reactions of Bromoenones with Secondary Amino Alcohols

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 30, Pages 4202-4210

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800659

Keywords

Fluorinated compounds; Nitrogen heterocycles; Fused-ring systems; Small ring systems; Amino alcohols; Fluorine

Funding

  1. Russian Science Foundation [18-13-00136]
  2. Russian Science Foundation [18-13-00136] Funding Source: Russian Science Foundation

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Fluorinated -bromoenones react readily with amino alcohols containing a secondary amino group to give monocyclic morpholine derivatives or unexpected bicyclic compounds containing a morpholine moiety fused with an oxetane ring. The reactions are highly stereoselective. The assembly of these heterocycles starts with an aza-Michael addition followed by intermolecular substitution and addition processes.

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