Abstract:
Asymmetric aldol reactions of isatin and 4,6-dibromoisatin with acetone are efficiently catalyzed by β-amino alcohols derived from α-pinene and 3-carene. The target compounds can be isolated by crystallization from toluene, which eliminates the need for using chromatography and makes the asymmetric synthesis of (R)-convolutamydine A (up to 94% ee and yield 75%) simple and convenient.
Citation:
S. G. Zlotin, O. A. Banina, D. V. Sudarikov, A. A. Nigmatov, L. L. Frolova, A. V. Kutchin, “Asymmetric aldol reaction of isatins with acetone in the presence of terpene amino alcohols”, Mendeleev Commun., 30:2 (2020), 147–149
Linking options:
https://www.mathnet.ru/eng/mendc1129
https://www.mathnet.ru/eng/mendc/v30/i2/p147
This publication is cited in the following 7 articles:
Yao Yao, Yuan Yu, Ming-Liang Shi, Xin-Yue Fan, Ru-De Lin, Kun Li, Wen-Dian Li, Fei-Yan Tao, Na Wang, “Development of a photoenzymatic one-pot hybrid system for the direct synthesis of 3,3-disubstituted indole-2-ketones from N-methyl indoles”, Org. Chem. Front., 11:11 (2024), 3151
Deepa, Surendra Singh, “Prolinamide and Prolinamide Tagged with Ionic Liquid Intercalated in Bentonite Clay, a Recyclable Catalyst for Asymmetric Aldol Reactions”, ChemistrySelect, 8:1 (2023)
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
Polina A. Petrova, Denis V. Sudarikov, Larisa L. Frolova, Roman V. Rumyantcev, Svetlana A. Rubtsova, Aleksandr V. Kutchin, “Synthesis of Trifluoromethylated Monoterpene Amino Alcohols”, Molecules, 27:20 (2022), 7068
V. E. Filatov, D. A. Iuzabchuk, B. N. Tarasevich, N. V. Zyk, E. K. Beloglazkina, “A convenient E-diastereoselective synthesis of NH-isatin N′-arylimines via the aza-Wittig reaction”, Mendeleev Commun., 32:5 (2022), 634–636
Pei Wang, Yang Zhang, Hong Yang, Guo‐Rong Ma, Jin‐Bao Wang, Wen Yang, Zhi‐Hong Du, Chao‐Shan Da, “Enantioselective Cross‐Aldol Reaction with Ketones and Non‐Enolizable Ketones Catalyzed by Tetrapeptides”, ChemistrySelect, 6:30 (2021), 7722
Fatemeh Shams, Javad Mokhtari Aliabad, Morteza Rouhani, “Asymmetric cross-aldol reaction of isatin and ketones catalyzed by crude earthworm extract as efficient biocatalyst”, Green Chemistry Letters and Reviews, 13:3 (2020), 258
Contact us: