Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 25, Pages 8550-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja1033952
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Funding
- NSF [CHE-0969157]
- NIGMS [R01 GM084254]
- UCSB
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0969157] Funding Source: National Science Foundation
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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 a-oxo metal carbene chemistry without using hazardous diazo ketones.
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