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For important examples of asymmetrically substituted silicon moieties as chiral auxiliaries, see: a) G. L. Larson, V. Cruz de Maldonado, L. M. Fuentes, L. E. Torres, J. Org. Chem. 1988, 53, 633-639; b) B. F. Bonini, S. Masiero, G. Mazzanti, P. Zani, Tetrahedron Lett. 1991, 32, 6801-6804; c) M. Trzoss, J. Shao, S. Bienz, Tetrahedron 2002, 58, 5885-5894.
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For important examples of asymmetrically substituted silicon moieties as chiral auxiliaries, see: a) G. L. Larson, V. Cruz de Maldonado, L. M. Fuentes, L. E. Torres, J. Org. Chem. 1988, 53, 633-639; b) B. F. Bonini, S. Masiero, G. Mazzanti, P. Zani, Tetrahedron Lett. 1991, 32, 6801-6804; c) M. Trzoss, J. Shao, S. Bienz, Tetrahedron 2002, 58, 5885-5894.
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0037100515
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For important examples of asymmetrically substituted silicon moieties as chiral auxiliaries, see: a) G. L. Larson, V. Cruz de Maldonado, L. M. Fuentes, L. E. Torres, J. Org. Chem. 1988, 53, 633-639; b) B. F. Bonini, S. Masiero, G. Mazzanti, P. Zani, Tetrahedron Lett. 1991, 32, 6801-6804; c) M. Trzoss, J. Shao, S. Bienz, Tetrahedron 2002, 58, 5885-5894.
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For examples of attempted reagent control, see: a) J. L. Fry, M. G. Adlington, J. Am. Chem. Soc. 1978, 100, 7641-7644; b) P. J. Stang, A. E. Learned, J. Org. Chem. 1989, 54, 1779-1781.
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For examples of attempted reagent control, see: a) J. L. Fry, M. G. Adlington, J. Am. Chem. Soc. 1978, 100, 7641-7644; b) P. J. Stang, A. E. Learned, J. Org. Chem. 1989, 54, 1779-1781.
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a) For an excellent review on hydrosilylations including reaction mechanisms, see: I. Ojima, Z. Li, J. Zhu in The Chemistry of Organic Silicon Compounds, Vol. 2 (Eds.: Z. Rappoport, Y. Apeloig), Wiley, New York, 1998, pp. 1687-1792;
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b) For a review on asymmetric catalyst-controlled hydrosilylations, see: T. Hayashi in Comprehensive Asymmetric Catalysis, Vol. 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, pp. 319-333.
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17044385068
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Diploma Thesis, Albert-Ludwigs-Universität, Freiburg
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Earlier investigations from our laboratories support the assumption that formation of the carbon-hydrogen bond prior to the carbon-silicon bond is severely detrimental to efficient silicon-to-carbon chirality transfer: S. Rendler, Diploma Thesis, Albert-Ludwigs-Universität, Freiburg, 2004.
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0346122765
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a) For a modular and convergent approach to 1-sila-1,2,3,4- tetrahydronaphthalenes with silicon-centered chirality, see: M. Oestreich, U. K. Schmid, G. Auer, M. Keller, Synthesis 2003, 2725-2739;
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Synthesis
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Oestreich, M.1
Schmid, U.K.2
Auer, G.3
Keller, M.4
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30
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17044420127
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note
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b) HPLC analysis using a Daicel Chiralcel OD-H column (n-heptane at 20$C) for (R)-4 provided baseline separation of enantiomers (see also Table 1).
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31
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a) Co, Ni, Pd, Ir, Pt: L. H. Sommer, J. E. Lyons, H. Fujimoto, J. Am. Chem. Soc. 1969, 91, 7051-7061;
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Sommer, L.H.1
Lyons, J.E.2
Fujimoto, H.3
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17044392331
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note
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[8]
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35
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17044381376
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note
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a) Not suprisingly, all attempts directed towards chemical correlation of tBu-substituted cyclic silanes 8 and 10 by oxidative degradation have failed so far. Although the ROESY NMR experiments were not completely conclusive, we assigned the relative configurations of 10 and 8 (see Supporting Information for details). Based on these measurements, we suggest the relative configurations as depicted;
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36
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17044421359
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note
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b) HPLC analysis using two coupled Daicel Chiralcel OD-H columns (n-heptane at 0°C) for 7 provided baseline separation of enantiomers (see also Table 1).
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37
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17044416961
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note
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We are not aware of another example of a positive nonlinear effect in a transition-metal-catalyzed, reagent-controlled asymmetric transformation.
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