Skip to main content

Research Repository

Advanced Search

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

Baumann, Marcus; Baxendale, Ian R.

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


Authors

Marcus Baumann



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.

Files






You might also like



Downloadable Citations