Technology development of enantioselective addition of diethyl malonate to nitrostyrene



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Abstract

The 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.

About the authors

Alexander N Reznikov

Samara State Technical University

к.х.н., доцент; Самарский государственный технический университет; Samara State Technical University

Evgeniy V Golovin

Samara State Technical University

ассистент; Самарский государственный технический университет; Samara State Technical University

Yuriy N Klimochkin

Samara State Technical University

д.х.н., профессор; Самарский государственный технический университет; Samara State Technical University

References

  1. Thirumalaikumar M. Enantioselective Michael addition reactions // Org. Prep. & Proced. Int. - 2011. - Vol. 43. - № 1. - P. 67-129
  2. Grőger H. Catalytic enantioselective Strecker reactions and analogous synthesis // Chem. Rev. - 2003. - Vol. 103. - № 8. - P. 2795-2827.
  3. 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.
  4. Pellisier H. Asymmetric organocatalysis // Tetrahedron. - 2007. - Vol. 63. - № 38. - P. 9267-9331.
  5. 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.
  6. 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.
  7. 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.
  8. 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.
  9. 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.
  10. 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.
  11. 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.
  12. 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.

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Copyright (c) 2011 Reznikov A.N., Golovin E.V., Klimochkin Y.N.

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