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Fluoride-Mediated Desulfonylative Intramolecular Cyclization to Fused and Bridged Bicyclic Compounds: A Complex Mechanism.

Michelle BezansonAnna TombergNicolas Moitessier
Published in: The Journal of organic chemistry (2017)
We previously reported the synthesis of polysubstituted chiral oxazepanes in three steps from commercially available starting materials. The unexpected reaction of one of these 1,4-oxazepanes in the presence of TBAF provided a 4-oxa-1-azabicyclo[4.1.0]heptane core. This unusual process significantly increased the complexity of the molecular scaffold by introducing a bicyclic core. Surprisingly, the generated bicyclic structure featuring three stereocenters was a mixture of enantiomers with no other diastereomers observed. These striking experimental observations deserved further investigations. A combination of experimental and computational investigations unveiled a complex diastereoselective mechanism. Mechanistic rationale is presented for this observed rearrangement.
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