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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols
Longwu Ye1, Weimin He, Liming Zhang
1Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA.
Abstract:
A general solution for the synthesis of various oxetan-3-ones is developed. This reaction uses readily available propargylic alcohols as substrates and proceeds without the exclusion of moisture or air ("open flask"). Notably, oxetan-3-one, a highly valuable substrate for drug discovery, can be prepared in one step from propargyl alcohol in a fairly good yield. The facile formation of the strained oxetane ring provides strong support for the intermediacy of alpha-oxo gold carbenes. This safe and efficient generation of gold carbenes via intermolecular alkyne oxidation offers a potentially general entry into alpha-oxo metal carbene chemistry without using hazardous diazo ketones.
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