100765-41-1

Upstream product

• 4312-99-6 oct-1-en-3-one 
• 106-38-7 para-bromotoluene 
• 628-71-7 1-Heptyne 
• 88330-54-5 2-Methyl-5-pentyl-3-p-tolyl-isoxazolidine 

Relevant academic research and scientific papers

One-pot consecutive reactions based on the synthesis of conjugated enones by the re-catalysed meyer-schuster rearrangement

Re catalysis in one-pot reactions: An atom-economical, one-pot strategy that involves alkyne deprotonation and a subsequent rhenium(V)-catalysed Meyer-Schuster rearrangement of the alkynol to provide α,β- unsaturated enones in high yield has been developed (see scheme). Subsequent in situ hydride reduction or Diels-Alder reaction of the enones provided products in good-to-high overall yields. Copyright

Palladium-catalysed heck reactions of alk-1-en-3-ones with aryl bromides: A very simple access to (E)-1-arylalk-1-en-3-ones

When appropriate reaction conditions are used, very high yields of (E)-1-arylalk-1-en-3-one derivatives can be obtained by palladium-catalysed reactions of alk-1-en-3-ones with aryl bromides. The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane in combination with [Pd(C3H5)Cl]2 was found to be a very efficient catalyst for this reaction. In general, higher reaction rates were observed with electron-poor aryl bromides, but the electron-rich aryl bromides 1-bromo-4-(dimethylamino)benzene and 4-bromoanisole also led to the arylated enones in high yields. Even with sterically very congested aryl bromides such as 9-bromoanthracene, 1-bromo-2,4,6-trimethylbenzene or 1-bromo-2,4,6-triisopropylbenzene, the expected (E)-1-arylalk-1-en-3-ones were obtained in moderate to good yields. These enones appear to be unstable under the reaction conditions, and the addition of a small amount of hydroquinone to the reaction mixture was found to be crucial, especially for the vinylation of electron-deficient aryl bromides. A variety of alk-1-en-3-ones has been employed, and better results in terms of substrate/ catalyst ratios were obtained when oct-1-en-3-one or hex-1-en-3-one was used than when but-1-en-3-one or pent-1-en-3-one was used. It should be noted that several reactions can be performed with as little as 0.1-0.001 mol% catalyst. Georg Thieme Verlag Stuttgart.

N,O-HETEROCYCLES. XVI. DIRECT CONVERSION OF SOME ISOXAZOLIDINES INTO ALCOHOLS VIA α,β-ENONES

The 1,3-dipolar cycloadducts between nitrones and alkenes are converted into alcoholic derivatives by trimethyl phosphate and by subsequent reduction.The reaction of the substituted isoxazolidines, exempt of further functionalities, proceeds under the action of TMP through a sequence of steps including a Hofmann-like elimination with electronic-controlled orientation indicated also by thermochemical calculations.The overall process leads to the formation of saturated and unsaturated alcohols as known for the reduction step.