Palladium-catalyzed asymmetric allylic substitution in aqueous media using amphiphilic resin-supported MOP ligands

Tetrahedron Letters

Volumn 39, Issue 45, 1998, Pages 8303-8306

  Uozumi, Yasuhiro ^a   Danjo, Hiroshi ^a   Hayashi, Tamio ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIPHENYL 2 PROPENYLACETATE; 3 METHYL 2,4 PENTANEDIONE; AMPHOPHILE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0032487795     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01812-7     Document Type: Article

References (34)

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28. 26 + 31 (c 2.0 chloroform).
29. 10. EDCI = 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. HOBt = 1-hydroxybenzotriazole.
30. 11 The resin-bound amino acids were prepared by standard Fmoc procedure. For a recent review, see: Bunin, B. A. "Combinatorial Index" Academic Press, London, 1998, and references cited therein.
31. 12 A library of PEP-MOP ligands containing various chiral α-amino acids in their tether regions was prepared and used for optimization of the enantioselectivity and the catalytic activity, where (R)-L-1d-f turned out to be the best ligands in the present allylic substitution.
32. 13 Ananlysis of 5 for contents of palladium and phosphorus by ICP-atomic emmision spectroscopy showed the ratio of Pd/P = 1/1.
33. 14 The allylic alkylation of 6 with the sodium salt of 7 in THF in the presence of palladium-(R)-MeO-MOP (ref. 5a) complex (2 mol %) gave <5% yield of (R)-8 (57% ee) at 25 °C for 12 h.
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