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.
Citation:
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, “Diastereoselective cycloaddition of isatin azomethine ylides to 5-arylidene-2-thiohydantoins bearing 3-positioned chiral substituent”, Mendeleev Commun., 32:2 (2022), 221–223
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S. G. Zlotin, K. S. Egorova, V. P. Ananikov, A. A. Akulov, M. V. Varaksin, O. N. Chupakhin, V. N. Charushin, K. P. Bryliakov, A. D. Averin, I. P. Beletskaya, E. L. Dolengovski, Yu. H. Budnikova, O. G. Sinyashin, Z. N. Gafurov, A. O. Kantyukov, D. G. Yakhvarov, A. V. Aksenov, M. N. Elinson, V. G. Nenajdenko, A. M. Chibiryaev, N. S. Nesterov, E. A. Kozlova, O. N. Mart'yanov, I. A. Balova, V. N. Sorokoumov, D. A. Guk, E. K. Beloglazkina, D. A. Lemenovskii, I. Yu. Chukicheva, L. L. Frolova, E. S. Izmest'ev, I. A. Dvornikova, A. V. Popov, A. V. Kutchin, D. M. Borisova, A. A. Kalinina, A. M. Muzafarov, I. V. Kuchurov, A. L. Maksimov, A. V. Zolotukhina, “The green chemistry paradigm in modern organic synthesis”, Russian Chem. Reviews, 92:12 (2023), RCR5104
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K. V. Belyaeva, L. P. Nikitina, V. S. Gen', A. V. Kuzmin, A. V. Afonin, B. A. Trofimov, “A straightforward access to 2-hydroxyoxazino[3,2-f ]phenanthridines from phenanthridine, oxalylacetylenes and water”, Mendeleev Commun., 32:4 (2022), 439–442
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