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For achiral catalysis with sulfoxide ligands, see: (a) Haddad, Y. M. Y.; Henbest, H. B.; Husbands, J.; Mitchell, T. R. B.; Trocha-Grimshaw, J. J. Chem. Soc., Perkin Trans. I 1974, 596.
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0001425763
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For attempts showing low selectivities/reactivities: a
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For attempts showing low selectivities/reactivities: (a) James, B. R.; McMillan, R. S. Can. J. Chem. 1977, 55, 3927.
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(b) Khiar, N.; Fernandez, I.; Alcudia, F. Tetrahedron Lett. 1993, 34, 123.
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(c) Tokunoh, R.; Sodeoka, M.; Aoe, K.; Shibasaki, M. Tetrahedron Lett. 1995, 36, 8035.
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0027997952
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For somewhat better selectivities using sulfoxide/nitrogen or sulfoxide/phosphine chelates, see: a
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For somewhat better selectivities using sulfoxide/nitrogen or sulfoxide/phosphine chelates, see: (a) Allen, J. V.; Bower, J. F.; Williams, J. M. J. Tetrahedron Asymmetry 1994, 5, 1895.
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37049069973
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For Rh-catalysis with ligand systems that incorporate potentially ligating sulfoxide moieties, see: a
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For Rh-catalysis with ligand systems that incorporate potentially ligating sulfoxide moieties, see: (a) Kvintovics, P.; James, B. R.; Heil, B. J. Chem. Soc., Chem. Commun. 1986, 1810.
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For reviews, see: a
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For reviews, see: (a) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
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(b) Yoshida, K.; Hayashi, T. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005; 55.
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Miashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7933.
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33
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39649110477
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Alternatively, the present sulfinate (S or R) can be obtained in high yield in one step: Solladie, G.; Hutt, J.; Girardin, A. Synthesis 1987, 67, 173.
-
Alternatively, the present sulfinate (S or R) can be obtained in high yield in one step: Solladie, G.; Hutt, J.; Girardin, A. Synthesis 1987, 67, 173.
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34
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1942532931
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The synthesis of (M,S,S)-1 and (P,S,S)-1 has been reported: Clayden, J.; Kubinski, P. M.; Sammiceli, F.; Helliwell, M.; Diorazio, L. Tetrahedron 2004, 60, 4387.
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The synthesis of (M,S,S)-1 and (P,S,S)-1 has been reported: Clayden, J.; Kubinski, P. M.; Sammiceli, F.; Helliwell, M.; Diorazio, L. Tetrahedron 2004, 60, 4387.
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35
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39649090831
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Its enantiomer (M,S,S)-1 also reacts readily with the Rh precursor, whereas (M,R,R)-1 and (P,S,S)-1 do not react cleanly to give the corresponding complexes. In this case, the relative orientation of the tolyl groups on the sulfoxides hinder formation of the dimer.
-
Its enantiomer (M,S,S)-1 also reacts readily with the Rh precursor, whereas (M,R,R)-1 and (P,S,S)-1 do not react cleanly to give the corresponding complexes. In this case, the relative orientation of the tolyl groups on the sulfoxides hinder formation of the dimer.
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36
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0012456998
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Bunten, K. A.; Farrar, D. H.; Poe, A. J.; Lough, A. Organometallics 2002, 21, 3344.
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Bunten, K.A.1
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Otomaru, Y.; Okamoto, K.; Shintani, R.; Hayashi, T. J. Org. Chem. 2005, 70, 2503.
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J. Org. Chem
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Otomaru, Y.1
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38
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0001257694
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For comparative studies on the binding ability of sulfoxides to LTMs: (a) Pettinari, C.; Pellei, M.; Caviccio, G.; Crucianelli, M.; Panzeri, W.; Colapietro, M.; Cassetta, A. Organometallics 1999, 18, 555.
-
For comparative studies on the binding ability of sulfoxides to LTMs: (a) Pettinari, C.; Pellei, M.; Caviccio, G.; Crucianelli, M.; Panzeri, W.; Colapietro, M.; Cassetta, A. Organometallics 1999, 18, 555.
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(b) Evans, D. R.; Huang, M.; Seganish, W. M.; Fettinger, J. C.; Williams, T. L. Inorg. Chem. Commun. 2003, 6, 462.
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Evans, D.R.1
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0344065573
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(c) Dorta, R.; Rozenberg, H.; Shimon, L. J. W.; Milstein, D. Chem. Eur. J. 2003, 9, 5237.
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Dorta, R.1
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41
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0037190861
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(a) Urbaneja, L. M.; Alexakis, A.; Krause, N. Tetrahedron Lett. 2002, 43, 7887.
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Urbaneja, L.M.1
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Krause, N.3
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42
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39649116130
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Whether epimerization of the methyl group occurs during catalysis under the reaction conditions used is not clear at this stage
-
(b) Whether epimerization of the methyl group occurs during catalysis under the reaction conditions used is not clear at this stage.
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