Marcus Baumann
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. |
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