Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 898, Issue -, Pages -Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2019.120876
Keywords
Chiral P-alkene ligands; Phosphoramidites; Hemilability; Chiral macrocycle; trans-dinuclear palladium complex; Asymmetric allylic amination
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Funding
- Fonacit [G-2005000433, LAB-97000821]
- Universidad Simon Bolivar (USB)
- Friedrich-Alexander-Universitat
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Dibenzazepinyl dichlorophosphine 2 reacts with (R, R)-2,3-O-isopropylidene-threitol (3) in Et2O solution to afford gram-quantities of the enantiopure macrocylic phosphoramidite (all-R)-6, which may be seen as a formal dimer of classic phosphoramidite P-alkene hybrid ligands. Complexation experiments with PdCl2 reveal highly selective formation of the trans-dinuclear complex (all-R)-11. The corresponding bulkier and rigidly trans-eclipsed 1,4-diol (S, S)-bis-hydroximethyl-9,10-dihydro-9,10-ethaneanthracene (4) does not favor macrocycle formation and exclusively leads to the new dibenzazepinyl phsophormaidite P-alkene ligand 7, which in Pd-catalyzed asymmetric allylic amination comes the well-known 'privileged' binol-derived P-alkene analogue 1 close in terms of enantioselection. (C) 2019 Elsevier B.V. All rights reserved.
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