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

Autor:	V. A. Kalyazin, V. A. Vasin, Nikolay V. Somov, P. S. Petrov
Rok vydání:	2019
Předmět:	010405 organic chemistry Organic Chemistry Silver acetate Methyl vinyl sulfone 01 natural sciences Toluene Medicinal chemistry Cycloaddition Transition state 0104 chemical sciences chemistry.chemical_compound chemistry Impurity Stereoselectivity Triethylamine
Zdroj:	Russian Journal of Organic Chemistry. 55:426-435
ISSN:	1608-3393 1070-4280
DOI:	10.1134/s107042801904002x
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::eb23377cd382d08d7e372a987bc4eed4 https://doi.org/10.1134/s107042801904002x Zobrazit plný text záznamu Plný text ve formátu PDF