Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 6, Pages 3321-3331Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo502912m
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Funding
- Spanish Government (MINECO) [CTQ2012-35790, CTQ2011-22589, CTQ2013-40855-R]
- Aragon Government (research group E40)
- Aragon Government (research group E97)
- Aragon Government
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A practical Pd-catalyzed ortho-olefination of enantioenriched N-(SO2Py)-protected aryl-alanine and norephedrine derivatives with electron-deficient alkenes has been developed using N-fluoro-2,4,6-trimethylpyridinium triflate as the terminal oxidant. The reaction occurs efficiently with excellent monosubstitution selectivity and without loss of enantiopurity. This cross-coupling proved to be broad in scope, tolerating a variety of steric and electronic changes to both coupling partners. Removal of the directing group under mild conditions provides access to optically active tetrahydroisoquinoline-3-carboxylic acid derivatives (Tics) with good diastereocontrol and with very small erosion of enantiomeric purity.
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