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0030831034
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a) A. S. C. Chan, W. Hu, C.-C. Pai, C.-P. Lau, J. Am. Chem. Soc. 1997, 119, 9570-9571;
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Chan, A.S.C.1
Hu, W.2
Pai, C.-C.3
Lau, C.-P.4
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4
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0001486820
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b) T. V. RujanBabu, T. A. Ayers, G. A. Halliday, K. K. You, J. C. Calabrese, J. Org. Chem. 1997, 62, 6012-6028;
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Rujanbabu, T.V.1
Ayers, T.A.2
Halliday, G.A.3
You, K.K.4
Calabrese, J.C.5
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6
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0344280194
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Brunner and Wink used chiral diphosphite ligands based on carbohydrates and tartaric acid derivatives in Rh-catalyzed hydrogenations and obtained ee values of 1-34 %: a) H. Brunner, W. Pieronczyk, J. Chem. Res. Synop. 1980, 76;
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J. Chem. Res. Synop.
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Brunner, H.1
Pieronczyk, W.2
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7
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0001643484
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b) D. J. Wink, T. J. Kwok, A. Yee, Inorg. Chem. 1990, 29, 5006-5008.
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Inorg. Chem.
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Wink, D.J.1
Kwok, T.J.2
Yee, A.3
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9
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0026684953
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b) N. Sakai, K. Nozaki, K. Mashima, H. Takaya, Tetrahedron: Asymmetry 1992, 3, 583-586;
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(1992)
Tetrahedron: Asymmetry
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, pp. 583-586
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Sakai, N.1
Nozaki, K.2
Mashima, K.3
Takaya, H.4
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12
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0000233323
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e) G. J. H. Buisman, L. A. van der Veen, A. Klootwijk, W. G. J. de Lange, P. C. J. Kamer, P. W. N. M. van Leeuwen, D. Vogt, Organometallics 1997, 16, 2929-2939;
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Organometallics
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Buisman, G.J.H.1
Van Der Veen, L.A.2
Klootwijk, A.3
De Lange, W.G.J.4
Kamer, P.C.J.5
Van Leeuwen, P.W.N.M.6
Vogt, D.7
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13
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0032579540
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f) R. Kadyrov, D. Heller, R. Selke, Tetrahedron: Asymmetry 1998, 9, 329-340:
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(1998)
Tetrahedron: Asymmetry
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Kadyrov, R.1
Heller, D.2
Selke, R.3
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14
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25944471646
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g) E. Yu. Zhorov, K. N. Gavrilov, V. A. Pavlov, A. T. Teleshev, É. E. Nifant'ev, E. I. Klabunovskii, Izv. Akad. Nauk SSSR Ser. Khim. 1990, 1451-1452:
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(1990)
Izv. Akad. Nauk SSSR Ser. Khim.
, pp. 1451-1452
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Zhorov, E.Yu.1
Gavrilov, K.N.2
Pavlov, V.A.3
Teleshev, A.T.4
Nifant'ev, E.E.5
Klabunovskii, E.I.6
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15
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77956672958
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h) J. Sakaki, W. B. Schweizer, D. Seebach, Helv. Chim. Acta 1993, 76, 2654-2665.
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(1993)
Helv. Chim. Acta
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, pp. 2654-2665
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Sakaki, J.1
Schweizer, W.B.2
Seebach, D.3
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16
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0003942864
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Wiley, New York
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meso Compounds such as cis-1,2-dimethylcyclohexane exist in the form of two chiral conformational enantiomers that rapidly interconvert: E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
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(1994)
Stereochemistry of Organic Compounds
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Eliel, E.L.1
Wilen, S.H.2
Mander, L.N.3
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17
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0030957928
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[4e.f] See also K. Nozaki, N. Sakai, T. Nanno, T. Higashijima, S. Mano, T. Horiuchi, H. Takaya, J. Am. Chem. Soc. 1997, 119, 4413-4423.
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J. Am. Chem. Soc.
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Nozaki, K.1
Sakai, N.2
Nanno, T.3
Higashijima, T.4
Mano, S.5
Horiuchi, T.6
Takaya, H.7
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19
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0000010553
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b) Bakos et al. synthesized the corresponding 2,5-bis(diphenylphosphino)idite from ditosylated 1,4:3,6-dianhydro-D-mannite by means of double nucleophilic substitution under inversion of configuration with lithium diphenylphosphide and used this nonchelating diphosphane in the asymmetric Rh-catalized hydrogenation (ee = 21-58%): J. Bakos, B. Heil, L. Marko, J. Organomet. Chem. 1983. 253, 249-252.
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(1983)
J. Organomet. Chem.
, vol.253
, pp. 249-252
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Bakos, J.1
Heil, B.2
Marko, L.3
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20
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0344280193
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note
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These results were obtained with preformed catalysts. If the hydrogenation is carried out with catalysts formed in situ. no differences in selectivity are observed. Both ligands lead to similarly high conversions and selectivities, the results for the S-selective ligand 4b being subject to variation: 4b (conversion 73-98%; ee = 89-95% (S)); 4c (conversion >99%: ee = 93.5% (R)). In contrast, the hydrogenation with 4e leads to identical results with catalyst formed in situ and with preformed catalyst.
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21
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0001670062
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S. D. Pastor, S. P. Shum, R. K. Rodehaugh, A. D. Debellis, F. H. Clarke, Helv. Chim. Acta 1993, 76, 900-914.
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(1993)
Helv. Chim. Acta
, vol.76
, pp. 900-914
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Pastor, S.D.1
Shum, S.P.2
Rodehaugh, R.K.3
Debellis, A.D.4
Clarke, F.H.5
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22
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0345574153
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note
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Detailed kinetic studies are under way in cooperation with T. Rosner and D. Blackmond (Max-Planck-Institut für Kohlenforschung).
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23
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85088333083
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note
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31P NMR signal.
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24
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0344280192
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note
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The force-field calculations were carried out with the SYBYL program (Tripos Ass. Inc.). Other than the lowest energy pair of enantiomers 7a/7b. no minimum was found for an achiral conformer. We thank Dr. K. Angermund for performing the calculations.
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