Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 41, Pages 14655-14663Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201603532
Keywords
allylic substitution; dynamic kinetic asymmetric transformations; enantioselectivity; phenol; rhodium
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Funding
- DFG
- Alexander von Humboldt Foundation
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Inspired by the mechanistic studies of rhodium-catalyzed atom-economic addition of carboxylate acids to allenes, a rhodium-catalyzed dynamic kinetic asymmetric allylation of different nucleophiles with racemic allylic carbonates has been developed. High regio- and enantioselectivities can be obtained under neutral conditions and, furthermore, the chemoselectivities can be controlled by different diphosphine ligands. (R,R)-QuinoxP* leads to selective O-allylation of phenols, whereas when embedding (S,S)-DIOP as the ligand, 2-naphthol is ortho-C-allylated for the first time in high enantioselectivity. To this end, hydroxypyridines can be N-allylated by Rh-I/(S)-DTBM-Segphos via the same intermediate as in the previously reported atom-economic addition to allenes.
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