65173-40-2

Upstream product

• 140-88-5 ethyl acrylate 
• 110-83-8 cyclohexene 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 1192-88-7 1-cyclohexene-1-carboxaldehyde 
• 22822-85-1 ethyl sodiodiethylphosphonoacetate 

Downstream Products

• 910310-52-0 (E)-3-(cyclohex-1-en-1-yl)prop-2-en-1-ol 
• 137151-57-6 (E)-3-(1-cyclohexenyl)-2-propenyl 1-(trimethylsilyl)vinyl ether 
• 137151-65-6 (R)-3-Cyclohex-1-enyl-1-trimethylsilanyl-pent-4-en-1-one 
• 137151-65-6 (S)-3-(1-cyclohexenyl)-1-(trimethylsilyl)-4-penten-1-one 
• 89244-64-4 C₉H₁₄O 

Relevant academic research and scientific papers

Ring Expansion, Ring Contraction, and Annulation Reactions of Allylic Phosphonates under Oxidative Cleavage Conditions

Oxidative cleavage of cycloalkenylalkylphosphonates 1 followed by treatment with base gives rise to homologated cycloalkenones 2 in good to excellent yields. Subjecting cycloalk-2-enylphosphonates 3 to identical conditions provides the one-carbon ring-contracted compounds 4 in excellent yields. Oxidative cleavage of γ,δ-unsaturated ketophosphonates 6 followed by treatment with base affords 2-cyclopenten-1-ones 7 in good overall yields. This method may offer a practical alternative to existing methods for effecting one-carbon ring expansion, ring contraction, and annulation reactions.

Ligand-accelerated non-directed C-H functionalization of arenes

The directed activation of carbon-hydrogen bonds (C-H) is important in the development of synthetically useful reactions, owing to the proximity-induced reactivity and selectivity that is enabled by coordinating functional groups. Palladium-catalysed non-directed C-H activation could potentially enable further useful reactions, because it can reach more distant sites and be applied to substrates that do not contain appropriate directing groups; however, its development has faced substantial challenges associated with the lack of sufficiently active palladium catalysts. Currently used palladium catalysts are reactive only with electron-rich arenes, unless an excess of arene is used, which limits synthetic applications. Here we report a 2-pyridone ligand that binds to palladium and accelerates non-directed C-H functionalization with arene as the limiting reagent. This protocol is compatible with a broad range of aromatic substrates and we demonstrate direct functionalization of advanced synthetic intermediates, drug molecules and natural products that cannot be used in excessive quantities. We also developed C-H olefination and carboxylation protocols, demonstrating the applicability of our methodology to other transformations. The site selectivity in these transformations is governed by a combination of steric and electronic effects, with the pyridone ligand enhancing the influence of sterics on the selectivity, thus providing complementary selectivity to directed C-H functionalization.

A 2-carbonyl-4-olefin-5-bromo -1,3-oxazine and the application of the synthetic method of the compound of (by machine translation)

The present invention provides 2-carbonyl-4-olefin-5-bromo -1,3-oxazine compounds and its synthetic method and application. The method comprises: the trifluoromethane sulfonic acid scandium/phosphorus-oxygen ligand and partially under the action of the so

The Meyer-Schuster rearrangement of ethoxyalkynyl carbinols

The combination of electron-rich alkoxyacetylenes and cationic gold catalysts provides excellent reactivity for the Meyer-Schuster rearrangement under mild conditions. Optimization of the reaction conditions with respect to stereoselectivity and investigations into the scope and mechanism of the rearrangement of secondary ethoxyalkynyl carbinols (γ-ethoxy-substituted propargyl alcohols) to α,β-unsaturated esters are described. Georg Thieme Verlag Stuttgart.

Enantioselective activation of ethers by chiral organoaluminum reagents: Application to asymmetric Claisen rearrangement

The asymmetric Claisen rearrangement of allyl vinyl ethers has been effected with a chiral organoaluminum reagent, (R)-1 or (S)-1 as an example of the enantioselectie activation of ether substrates. This method provides a facile asymmetric synthesis of various acylsilanes and acylgermanes with high optical purity. Among various trialkylsilyl substituents of chiral organoaluminum reagent 1, use of the more bulky t-butyldiphenylsilyl group exhibits the highest enantioselectivity. The conformational analysis of two possible chairlike transition-state structures of an allyl vinyl ether substrate reveals that a chiral organoaluminum reagent 1 can discriminate between these two conformations only by a difference in the orientation of α-methylene groups of ethers.