Palladium-catalyzed synthesis of N-aryloxazolidinones from aryl chlorides

Organic Letters

Volumn 5, Issue 13, 2003, Pages 2207-2210

  Ghosh, Arun ^a   Sieser, Janice E ^a   Riou, Maxime ^a   Cai, Weiling ^a   Rivera Ruiz, Luis ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINOALCOHOL; BASE; KETONE DERIVATIVE; LIGAND; OXAZOLIDINONE DERIVATIVE; PALLADIUM; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; ARYLATION; CATALYST; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR BIOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0141629815     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034428p     Document Type: Article

References (50)

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42. For uses of Xantphos in C-N bond-forming reactions, see: (b) Guari, Y.; van Es, D. S.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron Lett. 1999, 40, 3789-3790. (c) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (d) Harris, M. C.; Geis, O.; Buchwald, S. L. J. Org. Chem. 1999, 64, 6019-6022. For a kinetic study of Xantphos/Pd-catalyzed amine arylation reactions, see: (e) Guari, Y.; van Strijdonck, G. P. F.; Boele, M. D. K.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Chem. Eur. J. 2001, 7, 475-482.
43. DPPF = 1,1-bis(diphenylphosphino)ferrocene, DPEphos = bis(2-diphenylphosphinophenyl)ether, BINAP = 2,2-bis(diphenylphosphino)-1,1-binaphthyl, Xantphos = 9,9-dimethyl-4,5-bis(diphenylphosphino) xanthene.
44. The alkoxide bases showed faster rates. However, lower yields were observed as a result of hydrolytic decomposition of oxazolidinone, as well as undesired N-arylation.
45. Enantiopure oxazolidinones were used for this study. Comparison of products from both antipodes by chiral HPLC (detailed in Supporting Information) showed complete retention of stereochemistry. Preservation of optical purity during Pd-catalyzed arylation of α-substituted amines has been reported by others. See: Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
46. 4, and concentrated in vacuo. The crude residue was purified by chromatography on silica gel using mixtures of ethyl acetate/hexanes as the eluent to obtain pure product (81%).
47. For similar reactivity of aryl bromides, see ref 12a.
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