Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 31, Pages 12853-12859Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202003271
Keywords
C(sp(3))-H activation; amino acids; olefins; palladium; synthetic methods
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Funding
- Scripps Research Institute (TSRI)
- NIH (NIGMS) [2R01GM084019]
- Korea Foundation for Advanced Studies (KFAS)
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Reported herein is the distal gamma-C(sp(3))-H olefination of ketone derivatives and free carboxylic acids. Fine tuning of a previously reported imino-acid directing group and using the ligand combination of a mono-N-protected amino acid (MPAA) and an electron-deficient 2-pyridone were critical for the gamma-C(sp(3))-H olefination of ketone substrates. In addition, MPAAs enabled the gamma-C(sp(3))-H olefination of free carboxylic acids to form diverse six-membered lactones. Besides alkyl carboxylic acids, benzylic C(sp(3))-H bonds also could be functionalized to form 3,4-dihydroisocoumarin structures in a single step from 2-methyl benzoic acid derivatives. The utility of these protocols was demonstrated in large scale reactions and diversification of the gamma-C(sp(3))-H olefinated products.
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