Publication Details:
Title: Lewis Acid-Driven Meyer–Schuster-Type Rearrangement of Yne-Dienone
| Author(s) | Rajendra K. Mallick, Tirumaleswararao Guntreddi, Nagarjuna Kommu , Vangara Srinivas and Akhila K. Sahoo* : J. Org. Chem. 2021, 86, 7059–7068. |
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| Journal Name | The Journal of Organic Chemistry |
| journal image URL | http://chemistry.uohyd.ac.in/~aks/wp-content/uploads/koushikjoc.png |
More Details:
Developed herein is a Cu(II)-catalyzed Meyer–Schuster-type rearrangement of alkyne-tethered cyclohexadienone for the construction of m-enone-substituted phenols. The reaction involves an uncommon 5-exo-trig 1,6-enyne cyclization of alkyne-tethered-cyclohexadienone, aromatization-triggered C–O bond cleavage, and an electrocyclic 4π-ring-opening of oxetene intermediate. This atom-efficient transformation provides access to a wide range of synthetically important α-(m-substituted phenol)-α,β-unsaturated ketones, featuring a broad scope with labile functional group tolerance. The gram-scale demonstration makes this transformation synthetically viable. The synthetic application of α,β-unsaturated ketones is also showcased.