Diastereoselective cycloaddition of isatin azomethine ylides to 5-arylidene-2-thiohydantoins bearing 3-positioned chiral substituent
Alexander A. Barashkin, V. S. Polyakov, Nikita L. Shikut’, Anastasia D. Putilova, Anton R. Gorovoy, Anton D. Degtiarev, В. А. Тафеенко, Boris N. Tarasevich, N. V. Zyk, Елена К. Белоглазкина
Abstract
1,3-Dipolar cycloaddition of azomethine ylide, generated from isatin and sarcosine, with 5-arylidene-2-thiohydantoins equipped with various chiral substituents at the N3 atom occurs diastereoselectively. The highest selectivity with dr = 5 : 1 was observed for the 2-thiohydantoin bearing 1,2-diphenylethyl substituent.
Topics & Concepts
Azomethine ylideChemistrySubstituentIsatinCycloadditionSarcosineSelectivityCarbon atomMedicinal chemistryPyrrolidineStereochemistry1,3-Dipolar cycloadditionOrganic chemistryRing (chemistry)CatalysisGlycineBiochemistryAmino acidOrganic Chemistry Cycloaddition ReactionsSynthesis and Catalytic ReactionsSynthesis of heterocyclic compounds