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Reaction of Methyl Vinyl Sulfone with Schiff Bases Derived from α-Alanine Methyl Ester and Aromatic Aldehydes

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Abstract

Schiff bases derived from α-alanine methyl ester and aromatic aldehydes reacted with methyl vinyl sulfone in toluene at 20°C in the presence of silver acetate and 1.5 equiv of triethylamine to give the corresponding 1,3-dipolar cycloaddition products, methyl (2S*,4S*,5S*)-5-aryl-4-methanesuffonylpyrrolidine-2-carboxylates containing a small impurity (8–25%) of diastereoisomeric (2S*,4R*,5S*)-5-aryl-4-methanesulfonylpyrrolidine-2-carboxylates. The same compounds were formed when the reaction was carried out in boiling toluene, but in this case the (4S*)-diastereoisomer was the minor product. The stereoselectivity of the cycloaddition reactions was interpreted by DFT/PBE calculations of the energies of the final products and transition states.

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Authors and Affiliations

  1. Ogarev Mordovian State National Research University, Saransk, Russia

    V. A. Vasin, V. A. Kalyazin & P. S. Petrov

  2. Lobachevskii State University of Nizhny Novgorod, Nizhny Novgorod, Russia

    N. V. Somov

Authors
  1. V. A. Vasin
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  2. V. A. Kalyazin
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  3. P. S. Petrov
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  4. N. V. Somov
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Corresponding author

Correspondence to P. S. Petrov.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 4, pp. 513–523.

Deceased.

Funding

This study was performed in part in the framework of the base part of state assignment for higher educational and research institutions in the sphere of research activity (project no. 3.6502.2017/BCh).

Conflict of Interests

The authors declare the absence of conflict of interests.

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Vasin, V.A., Kalyazin, V.A., Petrov, P.S. et al. Reaction of Methyl Vinyl Sulfone with Schiff Bases Derived from α-Alanine Methyl Ester and Aromatic Aldehydes. Russ J Org Chem 55, 426–435 (2019). https://doi.org/10.1134/S107042801904002X

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  • DOI: https://doi.org/10.1134/S107042801904002X

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