4.8 Article

Rearrangements of Propargylic Esters Can Be Induced by Some Electrophiles

Journal

ORGANIC LETTERS
Volume 16, Issue 8, Pages 2260-2263

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol5007778

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Funding

  1. European Social Fund under the Global Grant measure [VP1-3.1-SMM-07-K-01-002]

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An electrophile-induced rearrangement of propargylic esters without need of transition catalysis is possible. In particular, this observation provides a mild, economic, and effective method for the introduction of benzyl ether derivatives to access functionalized alpha,beta-unsaturated ketones. Preliminary mechanistic studies suggest that this rearrangement undergoes an intramolecular 1,3-acyloxy shift.

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