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Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols.

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.

SUBMITTER: Ye L

PROVIDER: S-EPMC2904605 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols.

Ye Longwu L He Weimin W Zhang Liming L

Journal of the American Chemical Society 20100601 25

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 ...[more]

PMID: 20521793

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