Enantioselective synthesis in continuous flow : polymer supported isothiourea-catalyzed enantioselective Michael addition-cyclization with α-azol-2-ylacetophenones
Date
17/05/2024Grant ID
EP/W007517/1
EP/T023643/1
EP/T023643/1
EP/W007517/1
Keywords
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Show full item recordAbstract
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.
Citation
Zhou , Z , Kasten , K , Kang , T , Cordes , D B & Smith , A D 2024 , ' Enantioselective synthesis in continuous flow : polymer supported isothiourea-catalyzed enantioselective Michael addition-cyclization with α-azol-2-ylacetophenones ' , Organic Process Research & Development , vol. 28 , no. 5 , pp. 2041–2049 . https://doi.org/10.1021/acs.oprd.4c00113
Publication
Organic Process Research & Development
Status
Peer reviewed
ISSN
1083-6160Type
Journal article
Description
Engineering and Physical Sciences Research Council - EP/W007517, EP/T023643/1Collections
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