Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 33, Pages 8682-8686Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201402665
Keywords
multicomponent reactions; photocaging; protecting groups; synthetic methods; water chemistry
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Funding
- Ministry of Education, Culture and Science [024.001.035]
- Royal Netherlands Academy of Sciences (KNAW academy chair)
- European Research Council (ERC) [227897]
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Photocaged compounds are important tools for studying and regulating multiple processes, including biological functions. Reported herein is the use of the Passerini multicomponent reaction for modular preparation of photocaged carboxylic acids. The reaction is compatible with several functionalities and proceeds smoothly both in water and dichloromethane. The choice of aldehyde determines the wavelength used for deprotection and enables formation of orthogonally protected products. The isocyanide component can be used for introduction of reactive tags and photosensitizers, as well as for immobilization on a solid support.
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