Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 34, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202207354
Keywords
C-H Activation; Carboxylic Acids; Lactamization; Ligand Design; Palladium
Categories
Funding
- NIH (NIGMS) [R01GM084019]
- Scripps Research Institute
- Bristol Myers Squibb
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In this study, a novel C-H functionalization reaction was reported, which utilizes common protecting groups and practical oxidants for the lactamization of tosyl-protected aliphatic amides. The reaction was enabled by a specific ligand and shows mild reaction conditions, good scalability, and the use of convenient oxidants and protecting groups. Further derivatization of the beta-lactam products allows the synthesis of various biologically significant compounds.
The development of C(sp(3))-H functionalization reactions that use common protecting groups and practical oxidants remains a significant challenge. Herein we report a monoprotected aminoethyl thioether (MPAThio) ligand-enabled beta-C(sp(3))-H lactamization of tosyl-protected aliphatic amides using tert-butyl hydrogen peroxide (TBHP) as the sole oxidant. This protocol features exceedingly mild reaction conditions, reliable scalability, and the use of practical oxidants and protecting groups. Further derivatization of the beta-lactam products enables the synthesis of a range of biologically important motifs including beta-amino acids, gamma-amino alcohols, and azetidines.
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