Asymmetric catalysis, part 91: Enantioselective monophenylation ofcis-1,2-cyclopentanediol with triphenylbismuth diacetate and chiral copper(II) complexes as catalysts

作者: H. Brunner , T. Chuard

DOI: 10.1007/BF00811078

关键词: Medicinal chemistrySelectivityCatalysisOrganic chemistryChemistryCopperOptically activeEnantioselective synthesisDiaminePyridineEnantiomer

摘要: The monophenylation ofcis-1,2-cyclopentanediol with triphenylbismuth diacetate in the presence of chiral Cu(II) complexes as catalysts gavecis-2-hydroxy-1-phenoxy-cyclopentane enantiomeric excesses up to 38%. optically active ligands used were triamine derivatives 2,6-bis(aminomethyl)pyridine and diamine 2-(aminomethyl)pyridine. Selectivity occurred only latter auxiliary ligands.

参考文章(23)
Henri Brunner, Uwe Obermann, Peter Wimmer, Asymmetrische katalysen: XXXII. Enantioselektive phenylierung von cis-cyclohexan-1,2-diol und meso-butan-2,3-diol Journal of Organometallic Chemistry. ,vol. 316, ,(1986) , 10.1016/0022-328X(86)82093-9
Carlo Botteghi, Alberto Schionato, Giorgio Chelucci, Henri Brunner, Alfred Kürzinger, Uwe Obermann, Asymmetrische katalysen: XLVI. Enantioselektive Hydrosilylierung von Ketonen mit [Rh(COD)Cl]2 und optisch aktiven Stickstoff-Liganden Journal of Organometallic Chemistry. ,vol. 370, pp. 17- 31 ,(1989) , 10.1016/0022-328X(89)87271-7
Klaus Bernauer, Robert Deschenaux, Toshiaki Taura, Stereoselectivity in reactions of metal complexes. VII: Asymmetric synthesis of amino acids by metal ion-promoted transamination Helvetica Chimica Acta. ,vol. 66, pp. 2049- 2058 ,(1983) , 10.1002/HLCA.19830660716
Henri. Brunner, Uwe. Obermann, Peter. Wimmer, Asymmetric catalysis. 44. Enantioselective monophenylation of diols with cupric acetate/pyridinyloxazoline catalysts Organometallics. ,vol. 8, pp. 821- 826 ,(1989) , 10.1021/OM00105A039
Derek H.R. Barton, Jean-Pierre Finet, Jamal Khamsi, Copper salts catalysis of N-phenylation of amines by trivalent organobismuth compounds Tetrahedron Letters. ,vol. 28, pp. 887- 890 ,(1987) , 10.1016/S0040-4039(01)81015-7
Derek H. R. Barton, Jean-Pierre Finet, Clotilde Pichon, The catalytic effect of copper ions in the phenylation reaction of david and thieffry Journal of The Chemical Society, Chemical Communications. pp. 65- 66 ,(1986) , 10.1039/C39860000065
Derek H. R. Barton, Jean-Pierre Finet, Charles Giannotti, Frank Halley, The chemistry of pentavalent organobismuth reagents. Part 7. The possible role of radical mechanisms in the phenylation process for bismuth(V), and related lead(IV), lodine(III), and antimony(V) reagents Journal of The Chemical Society-perkin Transactions 1. pp. 241- 249 ,(1987) , 10.1039/P19870000241
Derek H. R. Barton, Jean-Pierre Finet, William B. Motherwell, Clotilde Pichon, The chemistry of pentavalent organobismuth reagents. Part 8. Phenylation and oxidation of alcohols by tetraphenylbismuth esters Journal of The Chemical Society-perkin Transactions 1. pp. 251- 259 ,(1987) , 10.1039/P19870000251
Derek H. R. Barton, Neerja Yadav Bhatnagar, Jean-Claude Blazejewski, Brigitte Charpiot, Jean-Pierre Finet, David J. Lester, William B. Motherwell, M. Teresa Barros Papoula, Stephen P. Stanforth, Pentavalent organobismuth reagents. Part 2. The phenylation of phenols Journal of The Chemical Society-perkin Transactions 1. ,vol. 17, pp. 2657- 2665 ,(1985) , 10.1039/P19850002657