This article is cited in 16 papers

Communications

Diastereoselective cycloaddition of isatin azomethine ylides to 5-arylidene-2-thiohydantoins bearing 3-positioned chiral substituent

A. A. Barashkin, V. S. Polyakov, N. L. Shikut, A. D. Putilova, A. R. Gorovoy, A. D. Degtiarev, V. A. Tafeenko, B. N. Tarasevich, N. V. Zyk, E. K. Beloglazkina

Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation

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.

Keywords: azomethine ylide, chiral substituent, isatin, spirooxindole, spiro compound, thiohydantoin, diastereoselectivity.

Language: English

DOI: 10.1016/j.mencom.2022.03.022

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