Enantioselective synthesis in continuous flow: polymer supported isothiourea-catalyzed enantioselective Michael addition-cyclization with α-azol-2-ylacetophenones

Zhanyu Zhou, Kevin Kasten, Tengfei Kang, David Bradford Cordes, Andrew David Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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 languageEnglish
Pages (from-to)2041–2049
JournalOrganic Process Research & Development
Volume28
Issue number5
Early online date2 May 2024
DOIs
Publication statusPublished - 17 May 2024

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