Three-component assembly of multiply-substituted homoallylic alcohols and amines using a flow chemistry photoreactor
Authors
Blakemore, David
Pasau, Patrick
Change log
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.
Publication Date
2018-10-19
Online Publication Date
2018-10-01
Acceptance Date
2018-09-26
Keywords
0305 Organic Chemistry
Journal Title
Organic Letters
Journal ISSN
1523-7060
1523-7052
1523-7052
Volume Title
20
Publisher
American Chemical Society (ACS)
Sponsorship
Engineering and Physical Sciences Research Council (EP/K009494/1)
Engineering and Physical Sciences Research Council (EP/M004120/1)
European Commission Horizon 2020 (H2020) Future and Emerging Technologies (FET) (737266)
Engineering and Physical Sciences Research Council (EP/K039520/1)
Engineering and Physical Sciences Research Council (EP/M004120/1)
European Commission Horizon 2020 (H2020) Future and Emerging Technologies (FET) (737266)
Engineering and Physical Sciences Research Council (EP/K039520/1)