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- Title
[2+2] Photocycloaddition of Cinnamates in Flow and Development of a Thiourea Catalyst.
- Authors
Telmesani, Reem; Park, Sung H.; Lynch-Colameta, Tessa; Beeler, Aaron B.
- Abstract
Cyclobutanes derived from the dimerization of cinnamic acids are the core scaffolds of many molecules with potentially interesting biological activities. By utilizing a powerful flow photochemistry platform developed in our laboratory, we have evaluated the effects of flow on the dimerization of a range of cinnamate substrates. During the course of the study we also identified a bis(thiourea) catalyst that facilitates better reactivity and moderate diastereoselectivity in the reaction. Overall, we show that carrying out the reaction in flow in the presence of the catalyst affords consistent formation of predictable cyclobutane diastereomers.
- Subjects
PHOTOCYCLOADDITION; ORGANOSULFUR compounds; THIOUREA; UREA compounds; DIAFENTHIURON
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 39, p11683
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201504454