Call us toll-free

Rathman Oxetan-3-one: Chemistry and Synthesis

ChemInform Abstract: Oxetan‐3‐one: Chemistry and Synthesis

Approximate price

Pages:

275 Words

$19,50

ChemInform Abstract: Oxetan-3-one: Chemistry and Synthesis

In conclusion, we have developed a general solution for the synthesis of various oxetan-3-ones. 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 α-oxo gold carbenes. This efficient generation of gold carbenes via intermolecular alkyne oxidation would potentially offer a general entry into α-oxo metal carbene chemistry without using hazardous diazo ketones.

Rathman Oxetan-3-one: Chemistry and Synthesis; ..

Synthesis of Enantiomerically Enriched 2-Benzyloxetan-3-one (4)aaee determined by chiral GC analysis of acetates formed by NaBH4 reduction and then acetylation of enantiomerically enriched and racemic ketone 4 (see the ).

Oxetan-3-one: chemistry and synthesis

3-Oxetanone Usage And Synthesis:

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 α-oxo gold carbenes. This safe and efficient generation of gold carbenes via intermolecular alkyne oxidation offers a potentially general entry into α-oxo metal carbene chemistry without using hazardous diazo ketones.

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 α-oxo gold carbenes. This safe and efficient generation of gold carbenes via intermolecular alkyne oxidation offers a potentially general entry into α-oxo metal carbene chemistry without using hazardous diazo ketones.

Get supplier listing of Oxetan-3-one and equal product

The methodology can be extended to the synthesis of a chiral 2,2-disubstituted oxetan-3-one in 90% ee by a one-pot double alkylation protocol, and a chiral C2 symmetric 2,4-disubstituted oxetan-3-one in 86% ee by controlled thermal isomerization of the hydrazone / configuration.

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 α-oxo gold carbenes. This safe and efficient generation of gold carbenes via intermolecular alkyne oxidation offers a potentially general entry into α-oxo metal carbene chemistry without using hazardous diazo ketones.

Order now
  • Asymmetric synthesis of 2-substituted oxetan-3-ones …

    Organic Chemistry

  • SAMP/RAMP hydrazones of oxetan-3-one, ..

    Oxetan-3-one - ResearchGate

  • synthesis* Ethers, Cyclic/chemistry;

    3-Oxetanone - Wikipedia

Order now

Thieme E-Journals - Synthesis / Abstract

Indeed, as far as we are aware, there are no reports of enolate generation from oxetan-3-ones. We were encouraged, however, by a report by Fadel and co-workers who have demonstrated that the SAMP/RAMP hydrazones of cyclobutanone can be successfully lithiated and alkylated. In this paper, we demonstrate how a variety of chiral 2-substituted as well as 2,2- and 2,4-disubstituted oxetan-3-ones can be prepared by metalation/alkylation of the SAMP/RAMP hydrazones derived from oxetan-3-one, offering a practical route to these important medicinal chemistry building blocks.

carbon–carbon bond of oxetan-3-one in the presence of a nickel ..

Oxetan-3-ones contain a strained four-membered ring and possess considerable synthetic/medicinal utility. They have been incorporated into steroid skeletons, used to prepare oxetanocin derivatives, and converted into 3-aminooxetanes including 3-aminooxetane-3-carboxylic acid. Moreover, Rogers-Evans, Carreira and co-workers have shown that the oxetane ring can serve as a surrogate of a gem-dimethyl group, resemble a carbonyl group, and offer alternatives to 1,3-heteroatom-substituted cyclohexanes in spirocyclic structures in drug discovery; in these studies, the parent oxetan-3-one serves as an essential starting material for introducing the oxetane ring. However, synthesis of oxetan-3-ones typically demand multiple synthetic steps and/or highly functionalized substrates. For example, oxetan-3-one itself was prepared in 4 or 5 steps with 23% or 13% overall yield, respectively, highlighting the challenge of constructing this strained skeleton and the lack of efficient preparative methods.

synthesis of 2-substituted oxetan-3 ..

Expansion of this oxetanone formation chemistry to tertiary propargylic alcohols was initially met with low yields likely due to increased tendency of forming propargylic cations under the acidic reaction conditions. To overcome this problem, an electron-withdrawing carboxylate group was installed to the alkyne terminus. Expectedly, the gold catalysis proceeded much slower, and mild heating was required to complete the reaction within 24 h; moreover, the combination of 4-acetylpyridine N-oxide and IPrAuNTf2 worked better. As shown in , high to excellent yields were observed with various substrates. For asymmetric substrates, low diastereoselectivities were observed (entries 2 and 3).

Synthesis of O -Heterocycles - Organic Chemistry Portal

The synthetic utility of this chemistry is underscored by a one-step preparation of oxetan-3-one. As discussed above, the synthesis of this highly useful O-heterocycle, requires multiple steps and is low yielding. It is commercially available but expensive. To our delight, this volatile heterocycle was formed in 71% NMR yield directly from cheap propargyl alcohol following this chemistry, and the catalyst loading could be lowered to 1 mol % without much affecting the yield (); moreover, a 51% NMR yield was achievable with cheaper and less amounts of reagents and a higher substrate concentration. Coupled with a subsequent Wittig reaction upon simple workup or a Strecker reaction directly, this reaction led to oxetane derivatives 9 and 10 in 62% and 60% overall yields, respectively [5 mol % of (2-biphenyl)Cy2PAuNTf2 used].

Order now
  • Kim

    "I have always been impressed by the quick turnaround and your thoroughness. Easily the most professional essay writing service on the web."

  • Paul

    "Your assistance and the first class service is much appreciated. My essay reads so well and without your help I'm sure I would have been marked down again on grammar and syntax."

  • Ellen

    "Thanks again for your excellent work with my assignments. No doubts you're true experts at what you do and very approachable."

  • Joyce

    "Very professional, cheap and friendly service. Thanks for writing two important essays for me, I wouldn't have written it myself because of the tight deadline."

  • Albert

    "Thanks for your cautious eye, attention to detail and overall superb service. Thanks to you, now I am confident that I can submit my term paper on time."

  • Mary

    "Thank you for the GREAT work you have done. Just wanted to tell that I'm very happy with my essay and will get back with more assignments soon."

Ready to tackle your homework?

Place an order