27750-19-2Relevant academic research and scientific papers
Chromium(II)-Catalyzed Diastereoselective and Chemoselective Csp2-Csp3 Cross-Couplings Using Organomagnesium Reagents
Li, Jie,Ren, Qianyi,Cheng, Xinyi,Karaghiosoff, Konstantin,Knochel, Paul
supporting information, p. 18127 - 18135 (2019/11/19)
A simple protocol for performing chromium-catalyzed highly diastereoselective alkylations of arylmagnesium halides with cyclohexyl iodides at ambient temperature has been developed. Furthermore, this ligand-free CrCl2 enables efficient electrophilic alkenylations of primary, secondary, and tetiary alkylmagnesium halides with readily available alkenyl acetates. Moreover, this chemoselective C-C coupling reaction with stereodefined alkenyl acetates proceeds in a stereoretentive fashion. A wide range of functional groups on alkyl iodides and alkenyl acetates are well tolerated, thus furnishing functionalized Csp2-Csp3 coupling products in good yields and high diastereoselectivity. Detailed mechanistic studies suggest that the in situ generated low-valent chromium(I) species might be the active catalyst for these Csp2-Csp3 cross-couplings.
Reactions of 3,4-Dihydroisoquinolines with Enol Esters Derived from β-Ketoesters
Akhrem, A. A.,Borisov, E. V.,Chernov, Yu. G.
, p. 1132 - 1136 (2007/10/03)
1-(1-Ethoxycarbonyl-2-oxopropyl)-2-acyltetrahydroisoquinolines were synthesized by reaction of 3,4-dihydroisoquinolines with 3-acyloxy-2-butenoates.In a similar way, reactions of 6,7-dimethoxy-3,4-dihydroisoquinoline with 3-acyloxy-2-pentenedioates yield mixtures of 2-(2-acyl-6,7-dimethoxytetrahydroisoquinolin-1-yl)-3-oxopentanedioates and 2,4-bis(2-acyl-6,7-dimethoxytetrahydroisoquinolin-1-yl)-3-oxopentanedioates.According to 1H NMR spectra, the compounds prepared exist in CDCl3 as an equilibrium mixture of isomers.A possible mechanism of transformation is discussed.
Stereochemical Imperative in Enzymic Decarboxylations. Stereochemical Course of the Decarboxylation Catalyzed by Acetoacetate Decarboxylase
Rozzel, Jr. David J.,Benner, Steven A.
, p. 4937 - 4941 (2007/10/02)
The stereochemical course of the decarboxylation of acetoacetate catalyzed by the enzyme acetoacetate decarboxylase (AAD) has been studied by using samples of optically active 2-tritioacetoacetate, prepared by enzymatic oxidation of samples of enantiomeric pairs of diastereomeric 2-tritio-3-hydroxybutyrates.A correlation is proposed conneting the stereochemical course of enzymatic decarboxylation (retention or inversion) with the structure of the substrate.Acetoacetate decarboxylase was found to catalyze decarboxylation with net racemization.
