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Three-component assembly of multiply-substituted homoallylic alcohols and amines using a flow chemistry photoreactor

Published version
Peer-reviewed

Type

Article

Change log

Authors

Blakemore, David 
Pasau, Patrick 

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.

Description

Keywords

0305 Organic Chemistry

Journal Title

Organic Letters

Conference Name

Journal ISSN

1523-7060
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)