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[2+2] Photocycloaddition of Cinnamates in Flow and Development of a Thiourea Catalyst
Author(s) -
Telmesani Reem,
Park Sung H.,
LynchColameta Tessa,
Beeler Aaron B.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201504454
Subject(s) - cyclobutanes , cinnamates , chemistry , cyclobutane , thiourea , catalysis , cycloaddition , reactivity (psychology) , flow chemistry , diastereomer , photochemistry , combinatorial chemistry , organic chemistry , medicine , ring (chemistry) , alternative medicine , pathology
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.