88343-87-7Relevant academic research and scientific papers
Rhenium-catalyzed α-alkylation of enol acetates with alcohols or ethers
Umeda, Rui,Takahashi, Yuuki,Yamamoto, Takaaki,Iseki, Hideki,Osaka, Issey,Nishiyama, Yutaka
supporting information, p. 92 - 101 (2018/11/01)
When benzylic and allylic alcohols were treated with enol acetate in the presence of a catalytic amount of a rhenium complex, ReBr(CO)5, the carbon-carbon bond formation of the alcohols and enol acetate smoothly proceeded to give the corresponding ketones and aldehyde in moderate to good yields. For the reaction of allylic alcohols, γ,δ-unsaturated carbonyl compounds were obtained in good yields. When ethers were used instead of alcohols as the alkylated agent, two alkyl moieties on the ethers were utilized on the reaction.
An Organocatalytic Cope Rearrangement
Kaldre, Dainis,Gleason, James L.
supporting information, p. 11557 - 11561 (2016/10/24)
The first example of an organocatalytic Cope rearrangement is reported. Acyclic and cyclic acyl hydrazides catalyze the rearrangement of 1,5-hexadiene-2-carboxaldehydes via iminium ion formation. A correlation between ring size and catalyst activity was observed for the cyclic hydrazides, with seven- and eight-membered-ring catalysts being the most active. Diazepane carboxylate 5 c (10 mol %) catalyzed the rearrangement of a range of dienes at room temperature in acetonitrile using triflic acid as a co-catalyst. Preliminary proof of principle for asymmetric catalysis was provided by rearrangement of 3,3-dimethyl-7-phenyl-1,5-heptadiene-2-carboxaldehyde in the presence of a novel 7-substituted diazepane carboxylate.
Highly selective 1,6-addition of aryl boronic acids to α,β, γ,δ-unsaturated carbonyl compounds catalyzed by an indium complex
Nishimura, Takahiro,Yasuhara, Yuichi,Hayashi, Tamio
, p. 5164 - 5166 (2007/10/03)
(Chemical Equation Presented) Perfect control: The catalytic 1,6-addition of aryl boronic acids to electron-deficient dienes was realized by use of an iridium catalyst (see scheme). High yields of the corresponding δ-arylated carbonyl compounds were obtai
Highly regioselective [3,3] rearrangement of aliphatic allyl vinyl ethers catalyzed by a metalloporphyrin complex, Cr(TPP)Cl
Takanami, Toshikatsu,Hayashi, Mikiko,Iso, Kazuhiro,Nakamoto, Hirose,Suda, Kohji
, p. 9467 - 9474 (2007/10/03)
The Claisen rearrangement of simple aliphatic allyl vinyl ethers catalyzed by a metalloporphyrin, Cr(TPP)Cl, is described. The porphyrin-based Lewis acid catalyst can effectively accelerate the rearrangement via a concerted [3,3] pathway with a minimal degree of bond ionization of the substrates, providing the corresponding Claisen products in moderate to high yields and almost perfect regioselectivity at low catalyst loading.
Rhodium-catalyzed substitution of allylic carbonates with enoxysilanes
Muraoka,Matsuda,Itoh
, p. 8807 - 8811 (2007/10/03)
Substitution at the allylic position proceeds smoothly in rhodium-catalyzed reactions of allyl carbonates with enoxysilanes under almost neutral conditions to give γ,δ-unsaturated ketones in good to excellent yields. (C) 2000 Elsevier Science Ltd.
