586354-79-2Relevant academic research and scientific papers
Organocatalytic enantioselective γ-aminoalkylation of unsaturated ester: Access to pipecolic acid derivatives
Xu, Jianfeng,Jin, Zhichao,Chi, Yonggui Robin
, p. 5028 - 5031 (2013)
The direct γ-carbon functionalization of α,β-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic γ-carbon undergoes highly enantioselective additions to hydrazones. The resulting δ-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.
Stereoselective synthesis of analogs of natural isoprenoids based on the reaction of alkyl 4-dialkoxyphosphoryl-3-methylbut-2-enoates with aldehydes in ionic liquids and in an imidazolium salt - Benzene system
Zlotin,Kryshtal,Zhdankina,Belyakov,Serebryakov
, p. 659 - 664 (2004)
Condensation of alkyl 4-dialkoxyphosphoryl-3-methylbut-2-enoates with a number of aldehydes under the Horner - Emmons reaction conditions in 1-butyl-3-methylimidazolium hexafluorophosphate and tetrafluoroborate and in 1-butyl-3-methylimidazolium bromide - benzene and 1-butyl-2,3- dimethylimidazolium hexafluorophosphate - benzene systems was studied. The E/Z-stereoisomer ratio of the olefination products for the reaction carried out in ionic liquids was 3:1, which corresponds to the values attained previously in the KOH - benzene - Bu4nNBr (cat.) system. Quantum-chemical calculations were used to determine the averaged radii (r 0) of the [Bu4nN] and substituted imidazolium cations by means of the Gaussian 98 program package. The stereoselectivity of olefination in the KOH - PhH - phase-transfer catalyst system decreases with a decrease in the r0 value for the catalyst cation. The possibility of recovery and reuse of ionic liquids is demonstrated.
Oxidative γ-addition of enals to trifluoromethyl ketones: Enantioselectivity control via lewis acid/n-heterocyclic carbene cooperative catalysis
Mo, Junming,Chen, Xingkuan,Chi, Yonggui Robin
supporting information; experimental part, p. 8810 - 8813 (2012/07/02)
An oxidative γ-functionalization of enals under N-heterocyclic carbene (NHC) catalysis to give unsaturated δ-lactones is disclosed. Enantioselectivity control involving the relatively remote enal γ-carbon was achieved via Lewis acid [Sc(OTf)3 or combined Sc(OTf) 3/Mg(OTf)2] and NHC cooperative catalysis.
A New Synthesis of α,β-Unsaturated Carboxylic Esters Using Dialkyltelluronium Carbethoxymethylide
Osuka, Atsuhiro,Mori, Yasuo,Shimizu, Hirohito,Suzuki, Hitomi
, p. 2599 - 2602 (2007/10/02)
Dialkyltelluronium carbethoxymethylide was found to condense with a variety of carbonyl compounds to yield α,β-unsaturated carboxylic esters in good yields.
