86778-46-3Relevant academic research and scientific papers
Organocatalytic asymmetric Robinson annulation of α,β- unsaturated aldehydes: Applications to the total synthesis of (+)-palitantin
Hong, Bor-Cherng,Wu, Ming-Fun,Tseng, Hsing-Chang,Huang, Guo-Fong,Su, Cheng-Feng,Liao, Ju-Hsiou
, p. 8459 - 8471 (2008/02/13)
(Chemical Equation Presented) The highly enantioselective organocatalytic Robinson annulation of α,β-unsaturated aldehydes was achieved, catalyzed by L-proline and trialkylamines and providing the formal [4 + 2] cycloaddition adducts. Additionally, in some examples in the catalysis with diarylpyrrolinol silyl ethers, the reactions afforded the [4 + 2] adducts with high enantioselectivity (>99.5% ee). The structure of the adduct, obtained from the reaction of 3-methylbut-2-enal and (E)-3-(2-nitrophenyl)acrylaldehyde, was confirmed by X-ray analysis. The absolute configurations of some [4 + 2] cycloadducts were investigated, and the methodology was applied in the synthesis of (+)-palitantin.
CHEMISTRY OF ENOL ETHERS. LXII. DIENE CONDENSATION OF 1-TRIMETHYLSILYLOXY-1,3-DIENES WITH α,β-UNSATURATED ALDEHYDES
Makin, S. M.,Tung, Nguyen Fyong,Shavrygina, O. A.,Arshava, B. M.,Romanova, I. A.
, p. 640 - 645 (2007/10/02)
The diene condensation of 1-trimethylsilyloxy-1,3-dienes (1-trimethylsilyloxy-1,3-butadiene, 1-trimethylsilyloxy-2-methyl-1,3-pentadiene, 1-trimethylsilyloxy-3-methyl-1,3-butadiene) with α,β-unsaturated aldehydes (acrylic, crotonic) is regioselective, leading to the formation of the "ortho isomers," and the cis-adducts are obtained preferentially.When heated with 10percent hydrochloric acid, the mono- and dimethyl-substituted 1-formyl-2-trimethylsilyloxy-3-cyclohexenes obtained during the diene condensation give high yields of the corresponding substituted 1-formyl-1,3-cyclohexadienes.
