In equal contribution.
Feruloylbenzotriazole and Weinreb Amide as Bioinspired Building Blocks: A Reactivity Study towards O-, N-, S-, and C-Nucleophiles
Article first published online: 5 MAR 2014
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
European Journal of Organic Chemistry
Volume 2014, Issue 12, pages 2594–2611, April 2014
How to Cite
Roman, B. I., Monbaliu, J.-C., De Coen, L. M., Verhasselt, S., Schuddinck, B., Van Hoeylandt, E. and Stevens, C. V. (2014), Feruloylbenzotriazole and Weinreb Amide as Bioinspired Building Blocks: A Reactivity Study towards O-, N-, S-, and C-Nucleophiles. Eur. J. Org. Chem., 2014: 2594–2611. doi: 10.1002/ejoc.201301895
- Issue published online: 11 APR 2014
- Article first published online: 5 MAR 2014
- Manuscript Received: 20 DEC 2013
- Natural products;
- Biomimetic synthesis;
- Nucleophilic addition;
- Nitrogen heterocycles;
A versatile route for the conversion of ferulic acid into biologically relevant molecules is presented. The compatibility of a number of protection and activation strategies with the 1,2-addition of a variety of O-, N-, S-, and C-nucleophiles to ferulic acid is evaluated. In particular, this report contains the first systematic study of the addition of (hetero)aryllithium reagents to 3-phenylpropenoyl Weinreb amides. The relevance of this “bioinspired” method is illustrated by the synthesis of a number of natural products or analogues, such as zingerone, curcuminoids, and (heteroaryl) chalcones.