Three-component assembly of multiply-substituted homoallylic alcohols and amines using a flow chemistry photoreactor
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Journal Title
Organic Letters
ISSN
1523-7060
Publisher
American Chemical Society (ACS)
Volume
20
Issue
20
Pages
6569-6572
Type
Article
This Version
VoR
Metadata
Show full item recordCitation
Chen, Y., Blakemore, D., Pasau, P., & Ley, S. (2018). Three-component assembly of multiply-substituted homoallylic alcohols and amines using a flow chemistry photoreactor. Organic Letters, 20 (20), 6569-6572. https://doi.org/10.1021/acs.orglett.8b02907
Abstract
Oxadiazolines are bench-stable diazo precursors, which are activated under UV radiation in the presence of vinylboronic acids and aldehydes to enable a one-step three-component assembly of densely-functionalized homoallylic alcohols. Sub-stitution on all positions of the homoallylic alcohol product were achieved with high functional group tolerance. No catalyst or other additive was required to effect the reaction which proceeds at 20 ℃ over 40 minutes. Imines and indoles were also incorporated, giving access to homoallylic amines.
Sponsorship
EPSRC (EP/K009494/1)
EPSRC (EP/M004120/1)
European Commission Horizon 2020 (H2020) Future and Emerging Technologies (FET) (737266)
EPSRC (EP/K039520/1)
Identifiers
External DOI: https://doi.org/10.1021/acs.orglett.8b02907
This record's URL: https://www.repository.cam.ac.uk/handle/1810/288618
Rights
Attribution 4.0 International, Attribution 4.0 International
Licence URL: http://creativecommons.org/licenses/by/4.0/
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