Continuous-Flow Synthesis of 2H-Azirines and Their Diastereoselective Transformation to Aziridines

Baumann, Marcus; Baxendale, Ian R.

Abstract

Using continuous-flow techniques, a small collection of 2H-azirines was prepared from oxime precursors via mesylation and base-promoted cyclisation. The 2H-azirines were either isolated after in-line purification or derivatised into a selection of 2-substituted aziridines through a telescoped reaction sequence involving nitrile, trifluoromethyl, or hydride nucleophilic addition. Importantly, these 2-substituted aziridines were produced with high cis diastereoselectivity providing access to small chiral heterocyclic entities that hold promise for medicinal chemistry programs because of their druglike features.

Citation

Baumann, M., & Baxendale, I. R. (2016). Continuous-Flow Synthesis of 2H-Azirines and Their Diastereoselective Transformation to Aziridines. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 27(01), 159-163. https://doi.org/10.1055/s-0035-1560391

• Journal Article Type: Article
• Acceptance Date: Nov 30, 2015
• Online Publication Date: Dec 1, 2015
• Publication Date: Jan 1, 2016
• Deposit Date: Dec 1, 2015
• Publicly Available Date: Dec 1, 2016
• Journal: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry
• Print ISSN: 0936-5214
• Electronic ISSN: 1437-2096
• Publisher: Thieme Gruppe
• Peer Reviewed: Peer Reviewed
• Volume: 27
• Issue: 01
• Pages: 159-163
• DOI: https://doi.org/10.1055/s-0035-1560391
• Keywords: Flow synthesis, Heterocycles, Azirine, Aziridine, Microreactor, Monolith, In-line purification.
• Public URL: https://durham-repository.worktribe.com/output/1397042