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Synthesis of (-) Baclofen as a Neurotransmitter Inhibitor

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Author Affiliations

  • 1Department of Chemistry, MNG Science College Babhulgaon-445101, India
  • 2Department of Chemistry, Savitribai Phule University of Pune-411007, India
  • 3Department of Chemistry, MNG Science College Babhulgaon-445101, India
  • 4Department of Chemistry, Savitribai Phule University of Pune-411007, India

Res.J.chem.sci., Volume 6, Issue (8), Pages 6-9, August,18 (2016)

Abstract

Here, we reports enantioselective Michael additions reaction of diethyl malonate with substituted styrene. The yield ranges from 80-65 % having enantioselectivity 80-95%. The present strategy useful for the synthesis (-)-Baclofen. Starting from commercially available 4-chlorobenzaldehyde.

References

  1. Kristina Wilckens, Marcel-Antoine Duhs, Dieter Lentz and Czekelius Constantin (2011)., Chiral 1,1_-Bi(tetrahydroisoquinoline)-Type Diamines as Efficient Ligands for Nickel-Catalysed Enantioselective Michael Addition to Nitroalkenes., Eur. J. Org. Chem., (28), 5441-5446.
  2. Tsubasa Inokuma, Masaya Furukawa, Takuya Uno, Yusuke Suzuki, Kohzo Yoshida, Yoshiaki Yano, Katsumi Matsuzaki and Takemoto Yoshiji (2011)., Bifunctional Hydrogen-Bond Donors That Bear a Quinazoline or Benzothiadiazine Skeleton for Asymmetric Organocatalysis., Chem. Eur. J., 17(37), 10470-10477.
  3. Jin-ming Liu, Xin Wang, Ze-mei Ge, Qi Sun, Tie-ming Cheng and Run-tao Lii (2011)., Solvent-free organocatalytic Michael addition of diethyl malonate to nitroalkenes: the practical synthesis of Pregabalin and γ-nitrobutyric acid derivatives., Tetrahedron, 67(3), 636-640.
  4. Laurence Menguy and Francois Couty (2010)., Azetidine-derived bifunctional organocatalysts for Michael reactions., Tetrahedron: Asymmetry., 21(19), 2385-2389.
  5. Diana Almaşi, Diego A. Alonso, Enrique Gómez-Bengoa and Carmen Nájera. (2009)., Chiral 2-Aminobenzimidazoles as Recoverable Organocatalysts for the Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes., J. Org. Chem. 74(16), 6163-6168.
  6. Patrick G. McGarraugh and Stacey E. Brenner. (2009)., Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition., Tetrahedron., 65(2), 449-455.
  7. David A. Evans, Shizue Mito, Daniel Seidel (2007)., Scope and Mechanism of Enantioselective Michael Additions of 1,3-Dicarbonyl Compounds to Nitroalkenes Catalyzed by Nickel(II)−Diamine Complexes., J. Am. Chem. Soc., 129(37), 11583-11592.
  8. Alessandra Lattanzi. (2006)., Enantioselective Michael addition of malonate esters to nitroolefins organocatalyzed by diaryl-2-pyrrolidinemethanols., Tetrahedron: Asymmetry. 17(5) 837-841.
  9. Masahiro Terada, Hitoshi Ube and Yusuke Yaguchi (2006)., Axially Chiral Guanidine as Enantioselective Base Catalyst for 1,4-Addition Reaction of 1,3-Dicarbonyl Compounds with Conjugated Nitroalkenes., J. Am. Chem. Soc., 128(5), 1454.
  10. Tomotaka Okino, Yasutaka Hoashi, Tomihiro Furukawa, Xuenong Xu and Yoshiji Takemoto (2005)., Enantio- and Diastereoselective Michael Reaction of 1,3-Dicarbonyl Compounds to Nitroolefins Catalyzed by a Bifunctional Thiourea., J. Am. Chem. Soc., 127(1), 119.
  11. Jinxing Ye, Darren J. Dixon, Peter S. Hynes (2005)., Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives., Chem.comm, 35, 4481-4485.
  12. Hongming Li, Yi Wang, Liang Tang, Li Deng (2004)., Highly Enantioselective Conjugate Addition of Malonate and β-Ketoester to Nitroalkenes: Asymmetric C−C Bond Formation with New Bifunctional Organic Catalysts Based on Cinchona Alkaloids., J. Am. Chem. Soc. 126(32), 9906-9907.