Rodionov reaction

Keywords aromatic aldehyde, primary amine, malonic acid monoethyl ester, Rodionov reaction, microwave irradiation, / -aryl-/ -amino acid ester, ethyl cinna-mate... 

Romanova [80] studied the effect of microwave irradiation on the direction and stereochemistry of the Rodionov reaction. Microwave irradiation of a mixture of equimolecular amounts of benzylammonium acetate 128, monoethyl malonate 130, and 2-phenylpropanal 127 resulted in the formation of yS-amino ester 132 in 38% yield and ethyl-4-phenyl-2-pentenoate 133 in 60% yield, exclusively as the trans isomer (Scheme 5.36). By contrast, thermal activation does not lead to forma-... 

The most important aspect of the synthesis of organic molecules that contain one or more stereogenic elements is usually that of stereochemical control. Indeed, such control is an essential aspect of the design of a good synthesis and, in addition, affects selection of the most appropriate method - including the choice of a particular route [83]. Several reports have described how microwave irradiation can be used to modify stereoselectivity in some reactions. The possibility of stereochemical modification by simply changing the mode of activation is a very attractive prospect. Slight modification of the stereoselectivity in the Rodionov reaction has been reported by Romanova [80]. 

Kinetics of Nucleophilic Substitution Reactions of Polyfluoroaromatic Compounds Rodionov, P P, Furin, G G J Fluorine Chem 47. 361 34 105 ... 

Kinetics of Nucleophilic Substitution Reactions of Polyfluoro Aromatic Compounds (Russ) Rodionov, PP, Funn, G G hv Sib Old Akad NaukSSSR 3-26 87 B- [Pg.21]

Rodionov VO, Fokin VV, Finn MG. Mechanism of the ligand-free Cu-I-catalyzed azide-alkyne cycloaddition reaction. Angew. Chem. Int. Ed. 2005 44 2210-2215. 

Rodionov and Chentsova (59) mention the foimation of hydrocotarnine and hydrohydrastinine by reaction of cotarnine and hydrastinine with caustic alkali, either per se or in a crossed Cannizzaro reaction with formaldehyde. 

The ethyl ester can also be prepared from ethyl acetoacetate (ethyl 3-oxobutanoate) by the method of Rodionov as well as via Steinkopf s method. Ethyl nitroacetate can be prepared in >70% yield from the dipotassium salt, ethanol, and sulfuric acid, with the addition of anhydrous magnesium sulfate in order to avoid the Nef reaction. The propyl and 2-propyl esters can also be obtained by this method. 

With the constant publications of new microbial genomic sequences, it can be inferred that several microorganisms do not produce Bj but possess (using in silica evaluations) the capacity to transport and utilize Bj2 (Rodionov et al. 2003), although it is not always clear in which reactions this vitamin is involved. 

Fokin AA, Yurchenko AG, Rodionov VN, Gunchenko PA, Yurchenko RI, Reichenberg A, Wiesner J, Hintz M, Jomaa H, Schreiner PR. Synthesis of the antimalarial drug FR900098 utilizing the nitroso-ene reaction. Org. Lett. 2007 9(21) 4379 382. 

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