Vestnik of Samara State Technical University. Technical Sciences SeriesVestnik of Samara State Technical University. Technical Sciences Series1991-85422712-8938Samara State Technical University1965510.14498/tech.2011.3.%uTechnology development of enantioselective addition of diethyl malonate to nitrostyreneReznikovAlexander Nк.х.н., доцент; Самарский государственный технический университет; Samara State Technical University-GolovinEvgeniy Vассистент; Самарский государственный технический университет; Samara State Technical University-KlimochkinYuriy Nд.х.н., профессор; Самарский государственный технический университет; Samara State Technical University-Samara State Technical University1509201119321922410022020Copyright © 2011, Samara State Technical University2011The new approach to the technology of enantioselective addition of diethyl malonate to nitrostyrene as key stage of obtaining of some fine organic synthesis intermediates is offered. It is shown that process can be carried out at a transition metal catalysis with high enantiomere excess of addition product.nitrostyrenediethyl malonateenantioselective additiontransition metal complexesнитростиролдиэтилмалонатэнантиоселективное присоединениекомплексы переходных металлов[Thirumalaikumar M. Enantioselective Michael addition reactions // Org. Prep. & Proced. Int. - 2011. - Vol. 43. - № 1. - P. 67-129][Grőger H. Catalytic enantioselective Strecker reactions and analogous synthesis // Chem. Rev. - 2003. - Vol. 103. - № 8. - P. 2795-2827.][1. А highly enantioselective organocatalyst for the Michael addition of cyclic ketones to nitroolefins / M.-K. Zhu, L.-F. Cun, A.-Q. Mi, Y.-Z Jiang, L.-Z.Gong // Tetrahedron: Asym. - 2006. - Vol. 17. - № 4. - P. 491-493.][Pellisier H. Asymmetric organocatalysis // Tetrahedron. - 2007. - Vol. 63. - № 38. - P. 9267-9331.][Chiral 2-aminobenzimidazoles as recoverable organocatalysts / D. Almasi, D.A. Alonso, E. Gomez-Bengoa, C. Najera // J. Org. Chem. - 2009. - Vol. 74. - № 16. - P. 6163-6168.][Hamashima Y., Hotta D., Sodeoka M. Direct Generation of Nucleophilic Chiral Palladium Enolate from 1,3-Dicarbonyl Compounds: Catalytic Enantioselective Michael Reaction with Enones // J. Am. Chem. Soc. - 2002. - Vol. 124. - № 38. - P. 11240-11241.][Kitajima H., Ito K., Katsuki T. A new methodology for the stereoselective synthesis of 4-substituted butenolides: Asymmetric Michael addition reaction of 2-(trimethylsilyloxy)furans to oxazolidinone enoates // Tetrahedron. - 1997. - Vol. 53. - № 50. - P. 17015-17028.][Desimoni G., Quadrelli P., Righetti P.P. Copper(II) in organic synthesis. VIII enantioselective michael reactions with chiral copper(II) complexes as catalysts // Tetrahedron. - 1990. - Vol. 46. - № 8. - P. 2927-2934.][Kanemasa S., Oderaotoshi Y., Wada E. Asymmetric Conjugate Addition of Thiols to a 3-(2-Alkenoyl)-2-oxazolidinone Catalyzed by the DBFOX/Ph Aqua Complex of Nickel(II) Perchlorate // J. Am. Chem. Soc. - 1999. - Vol. 121. - № 37. - P. 8675-8676.][1. Catalytic Enantioselective Conjugate Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes / J. Ji, D.M. Barnes, J. Zhang et al // J. Am. Chem. Soc. - 1999. - Vol. 121. - № 43. - P. 10215-10216.][Tandem Nazarov Cyclization-Michael Addition Sequence Catalyzed by an Ir(III) Complex / M. Janka, W. He, I.E. Haedicke // J. Am. Chem. Soc. - 2006. - Vol. 128. - № 16. - P. 5312-5313.][Evans D.A., Mito S., Seidel D. Scope and mechanism of enantioselective Michael additions of 1,3-dicarbonyl compounds to nitroalkenes catalyzed by nickel(II)-diamine complexes // J. Am. Chem. Soc. - 2007. - Vol. 129. - № 37. - P. 11583-11592.]