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Abstract
A packed reactor bed incorporating a polymer-supported isothiourea HyperBTM catalyst derivative has been used to promote the enantioselective synthesis of a range of heterocyclic products derived from α-azol-2-ylacetophenones and -acetamides combined with alkyl, aryl, and heterocyclic α,β-unsaturated homoanhydrides in continuous flow via an α,β-unsaturated acyl-ammonium intermediate. The products are generated in good to excellent yields and generally in excellent enantiopurity (up to 97:3 er). Scale-up is demonstrated on a 15 mmol scale, giving the heterocyclic product in 68% overall yield with 98:2 er after recrystallization.
Original language | English |
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Pages (from-to) | 2041–2049 |
Journal | Organic Process Research & Development |
Volume | 28 |
Issue number | 5 |
Early online date | 2 May 2024 |
DOIs | |
Publication status | Published - 17 May 2024 |
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Dive into the research topics of 'Enantioselective synthesis in continuous flow: polymer supported isothiourea-catalyzed enantioselective Michael addition-cyclization with α-azol-2-ylacetophenones'. Together they form a unique fingerprint.-
Allan Watson Programme Grant: Boron: Beyond the Reagent
Watson, A. J. B. (PI), Morris, R. E. (CoI), Smith, A. D. (CoI) & Zysman-Colman, E. (CoI)
1/05/23 → 30/04/28
Project: Standard
Datasets
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Enantioselective Synthesis in Continuous Flow: Polymer Supported Isothiourea Catalyzed Enantioselective Michael Addition-Lactamisation with Azaaryl ketones (dataset)
Smith, A. D. (Creator), Zhou, Z. (Creator), Kasten, K. (Creator), Kang, T. (Creator) & Cordes, D. B. (Creator), University of St Andrews, 15 Mar 2024
DOI: 10.17630/9eec7d03-0634-4239-ab47-bdfe105813ec
Dataset
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