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33748585522
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(c) Yamada, I.; Ohkouchi, M.; Yamaguchi, M.; Yamagishi, T. J. Chem. Soc., Perkin Trans. 1 1997, 1869-1873.
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0034722958
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(a) For hydrosilylation catalysts with high substrate generality, see: Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111-113.
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(b) For early work on hydrosilylation with mixed donor ligands, see: Brunner, H.; Reipl, G.; Weitzer, H. Angew. Chem., Int. Ed. Engl. 1983, 22, 331-332. Brunner, H.; Becker, R.; Reipl, G. Organometallics 1984, 3, 1354-1359.
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0001559784
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(b) For early work on hydrosilylation with mixed donor ligands, see: Brunner, H.; Reipl, G.; Weitzer, H. Angew. Chem., Int. Ed. Engl. 1983, 22, 331-332. Brunner, H.; Becker, R.; Reipl, G. Organometallics 1984, 3, 1354-1359.
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0001732693
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Ojima, I., Ed.; VCH Publishers: Weinheim
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(c) For reviews of asymmetric hydrosilylation, see: Nishiyama, H.; Itoh, K. Catalyctic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH Publishers: Weinheim, 2000, pp 111-143. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publisher: Weinheim, 1993; Chapter 6. Brunner, H. Transition Metals in Organic Synthesis; Beller, M., Ed.; Wiley-VCH: Weinheim, 1998; pp 131-140.
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0242559880
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Ojima, I., Ed.; VCH Publisher: Weinheim; Chapter 6
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(c) For reviews of asymmetric hydrosilylation, see: Nishiyama, H.; Itoh, K. Catalyctic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH Publishers: Weinheim, 2000, pp 111-143. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publisher: Weinheim, 1993; Chapter 6. Brunner, H. Transition Metals in Organic Synthesis; Beller, M., Ed.; Wiley-VCH: Weinheim, 1998; pp 131-140.
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16
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0000163020
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Beller, M., Ed.; Wiley-VCH: Weinheim
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(c) For reviews of asymmetric hydrosilylation, see: Nishiyama, H.; Itoh, K. Catalyctic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH Publishers: Weinheim, 2000, pp 111-143. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publisher: Weinheim, 1993; Chapter 6. Brunner, H. Transition Metals in Organic Synthesis; Beller, M., Ed.; Wiley-VCH: Weinheim, 1998; pp 131-140.
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Brunner, H.1
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17
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0001540849
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(d) Further advances have also been made in this area with titanocene catalysts, see: Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667-11670. Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640-5644.
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18
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0033597622
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(d) Further advances have also been made in this area with titanocene catalysts, see: Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667-11670. Yun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640-5644.
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(a) Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335-422.
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Appleton, T.G.1
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21
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0242392785
-
-
note
-
3; Z = 2; R = 0.0695, GooF = 1.149.
-
-
-
-
22
-
-
0242392784
-
-
note
-
3; Z = 4; R = 0.0276, GooF = 1.022.
-
-
-
-
23
-
-
0000945149
-
-
The tendency for sulfur substituents in palladium P/S chelate rings to adopt a pseudoaxial orientation has been previously noted. See: Barbaro, P.; Currao, A.; Herrmann, J.; Nesper, R.; Pregosin, P.; Salzmann, R. Organometallics 1996, 15, 1879-1888.
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Barbaro, P.1
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Nesper, R.4
Pregosin, P.5
Salzmann, R.6
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25
-
-
0242644549
-
-
note
-
2 gave 90% ee.
-
-
-
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27
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0030984990
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Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2801-2803.
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Iida, T.1
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28
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0035852020
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This hydrogenation was used in a synthesis of teicoplanin in our laboratory. Evans, D. A.; Katz, J. L.; Peterson, G. S.; Hintermann, T. J. Am. Chem. Soc. 2001, 123, 12411-12413.
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0032564850
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(b) Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635-1636.
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(c) Xiao, D.; Zhang, Z.; Zhang, X. Org. Lett. 1999, 1, 1679-1682.
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0034596334
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0000868533
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(a) Halpern, J. Science 1982, 217, 401-407.
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Halpern, J.1
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40
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0242392783
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note
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For an example where the rate-determining step appears to be migratory insertion, see ref 18.
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41
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0000733206
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(a) Allen, D. G.; Wild, B.; Wood, D. L. Organometallics 1986, 5, 1009-1015.
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33847085684
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46
-
-
0242476097
-
-
note
-
3; Z = 4; R = 0.0802, GooF = 1.219.
-
-
-
-
47
-
-
0242644546
-
-
note
-
3; Z = 2; R = 0.0369, GooF = 1.026.
-
-
-
-
48
-
-
33745336054
-
-
There has been some confusion because the quadrant diagram has been used both to correlate the catalyst structure with the product stereochemistry and also to predict or explain the structure of the catalyst-substrate complex (often incorrectly). Here we use it for the latter purpose. (a) Knowles, W. S. Acc. Chem. Res. 1983, 16, 106-112. (b) Komarov, I. V.; Börner, A. Angew. Chem., Int. Ed. 2001, 40, 1197-1200.
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Knowles, W.S.1
-
49
-
-
0035794970
-
-
There has been some confusion because the quadrant diagram has been used both to correlate the catalyst structure with the product stereochemistry and also to predict or explain the structure of the catalyst-substrate complex (often incorrectly). Here we use it for the latter purpose. (a) Knowles, W. S. Acc. Chem. Res. 1983, 16, 106-112. (b) Komarov, I. V.; Börner, A. Angew. Chem., Int. Ed. 2001, 40, 1197-1200.
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Komarov, I.V.1
Börner, A.2
-
50
-
-
0002285511
-
-
2 to the cis isomer is -2.5 kcal/mol, despite the greater steric interaction in the latter, See Chatt, J.; Wilkins, R. G. J. Chem. Soc. 1952, 4300-4306.
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J. Chem. Soc.
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Chatt, J.1
Wilkins, R.G.2
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51
-
-
0033607585
-
-
This has recently been claimed to be true for a bisphosphetane ligand on the basis of circumstantial evidence, but no structural data has been presented to bolster this claim. See Marinetti, A.; Jus, S.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 8365-8368. Some skepticism has been expressed as to their conclusions, see footnote 21 in Landis, C. R.; Feldgus, S. Angew. Chem., Int. Ed. 2000, 39, 2863-2866
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Marinetti, A.1
Jus, S.2
Genet, J.-P.3
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52
-
-
0034683083
-
-
This has recently been claimed to be true for a bisphosphetane ligand on the basis of circumstantial evidence, but no structural data has been presented to bolster this claim. See Marinetti, A.; Jus, S.; Genet, J.-P. Tetrahedron Lett. 1999, 40, 8365-8368. Some skepticism has been expressed as to their conclusions, see footnote 21 in Landis, C. R.; Feldgus, S. Angew. Chem., Int. Ed. 2000, 39, 2863-2866
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Angew. Chem. Int. Ed.
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Landis, C.R.1
Feldgus, S.2
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54
-
-
0242392781
-
-
note
-
3; Z = 5; R = 0.0310, GooF = 1.032.
-
-
-
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55
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33845279063
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(a) Burk, M. J.; McGrath, M. P.; Wheeler, R.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 5034-5039.
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84989085766
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58
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0032494440
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(b) Kimmich, B. F. M.; Somsook, E.; Landis, C. R. J. Am. Chem. Soc. 1998, 120, 10115-10125.
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59
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0242476095
-
-
note
-
Hydrides trans to the phosphorus donor generally have coupling constants of 80-100 Hz. See ref 31.
-
-
-
-
60
-
-
0242559874
-
-
note
-
3; Z = 2; R = 0.0314, GooF = 1.034.
-
-
-
-
61
-
-
0242559875
-
-
note
-
Although diastereomeric equilibration is not impossible, previous studies of iridium dihydrides have shown that isomerization only occurs above -50 °C. see refs 30, 31.
-
-
-
-
62
-
-
0242392780
-
-
note
-
We cannot eliminate the possibility that it is simply the predominance of the observed isomer, rather than its faster rate of reaction, that is responsible for the enantioselectivity.
-
-
-
-
63
-
-
37049083622
-
-
Note that the native selectivities of the P/S ligand and the substrate are reinforcing in these complexes, that is, the former prefers addition parallel to the thioether, and the latter prefers addition parallel to the olefin. See: Brown, J. M.; Maddox, J. J. Chem. Soc., Chem. Commun. 1987, 1278-1280.
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Brown, J.M.1
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0031979280
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For other mixed P/S ligands in asymmetric hydrosilylation, see: (a) Hiraoka, M.; Nishikawa, A.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull. 1998, 46, 704-706. (b) Nishibayashi, Y.; Segawa, K.; Singh, J. D.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370-379.
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0007023980
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For other mixed P/S ligands in asymmetric hydrosilylation, see: (a) Hiraoka, M.; Nishikawa, A.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull. 1998, 46, 704-706. (b) Nishibayashi, Y.; Segawa, K.; Singh, J. D.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370-379.
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For references on silane polymerization mechanisms, see: (a) Tilley, T. D.; Woo, H. G. Polym. Prepr. Am. Chem. Soc., Div. Polym. Chem. 1990, 31, 228-289. (b) Tilley, T. D. Comments Inorg. Chem. 1990, 10, 37-51.
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3743065867
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For references on silane polymerization mechanisms, see: (a) Tilley, T. D.; Woo, H. G. Polym. Prepr. Am. Chem. Soc., Div. Polym. Chem. 1990, 31, 228-289. (b) Tilley, T. D. Comments Inorg. Chem. 1990, 10, 37-51.
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0031566718
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For other hydrosilylation catalysts that display unusual temperature profiles, see: ref 39a and (a) Enders, D.; Gielen, H.; Breuer, K. Tetrahedron: Asymmetry 1997, 8, 3571-3574. (b) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398-409.
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For other hydrosilylation catalysts that display unusual temperature profiles, see: ref 39a and (a) Enders, D.; Gielen, H.; Breuer, K. Tetrahedron: Asymmetry 1997, 8, 3571-3574. (b) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics 1998, 17, 398-409.
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For other hydrosilylation catalysts displaying high enantioselectivity with alkyl ketones, see: Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111-113. Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486-5487.
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