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for complementary work, see reference [7d]
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K. Oisaki, Y. Suto, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 5644; for complementary work, see reference [7d].
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106
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0038475549
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[22] for pioneering work on a CuF-(S)-tolbinap-catalyzed enantioselective aldol reaction between silyl dienolate and aldehyde that involved a metalloenolate intermediate, see: a) J. Krüger, E. M. Carreira, J. Am. Chem. Soc. 1998, 120, 837;
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b) B. L. Pagenkopf, J. Krüger, A. Stojanovic, E. M. Carreira, Angew. Chem. 1998, 110, 3312;
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109
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33746231960
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note
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For a CuF-tolbinap-catalyzed enantioselective vinylogous Mukaiyama reaction on aliphatic ketones, see reference [7e].
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110
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0000493922
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unpublished results
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The complex was prepared according to a literature procedure: D. J. Gulliver, W. Levason, M. Webster, Inorg. Chim. Acta 1981, 52, 153; the amount of methanol molecules contained in the complex was determined by single-crystal X-ray crystallographic analysis of the complex (unpublished results).
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Inorg. Chim. Acta
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Gulliver, D.J.1
Levason, W.2
Webster, M.3
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111
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33746231957
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note
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[19c]
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112
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33746186942
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note
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A minor trace of phenylethanol (<1%), the product of reduction of acetophenone, was observed by GC analysis.
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113
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33746186938
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note
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Under the same conditions, without any additional ligand, 3 (1.25 mol%) gave only 20% conversion after a 2-hour reaction.
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114
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16244383506
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For the preparation, see: D. Tomita, R. Wada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 4138.
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Tomita, D.1
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115
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0001583703
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For the preparation of CuOtBu, see: T. Tsuda, T. Hashimoto, T. Saegusa, J. Am. Chem. Soc. 1972, 94, 658.
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Tsuda, T.1
Hashimoto, T.2
Saegusa, T.3
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116
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33746231956
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note
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Notably, no effect on the reaction rate was observed when using either preprepared CuOtBu or CuOtBu prepared in situ (from CuCl/NaOtBu); for a report on the salt effect on the rate of the enantioselective 1,4-reduction of β,β-disubstituted nitroalkenes when using both methods of CuOtBu preparation, see reference [20 h].
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117
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33746231958
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note
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For example, monodentate Feringa phosphonite, tridentate tBupybox, and tetradentate Trost ligand gave very low activity and/ or no enantioselectivity.
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118
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0000345787
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For original work, see: a) A. Togni, C. Breutel, A. Schnyder, F. Spindler, H. Landert, A. Tijani, J. Am. Chem. Soc. 1994, 116, 4062;
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Togni, A.1
Breutel, C.2
Schnyder, A.3
Spindler, F.4
Landert, H.5
Tijani, A.6
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119
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0001444993
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b) T. Ireland, G. Grossheimann, C. Wieser-Jeunesse, P. Knochel, Angew. Chem. 1999, 111, 1560;
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Ireland, T.1
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Knochel, P.4
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121
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These observations are in contrast to those usually made in other processes using taniaphos-derived ligands containing either alkyl or aromatic substituents on phosphorus atoms. Generally, a change from electron-rich aromatic groups to cyclohexyl groups has a negative effect on the enantioselectivity of the process. For some examples, see: a) B. L. Feringa, R. Badorrey, D. Peòa, S. R. Harutyunyan, A. J. Minnaard, Proc. Natl. Acad. Sci. USA 2004, 101, 5834;
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Feringa, B.L.1
Badorrey, R.2
Peòa, D.3
Harutyunyan, S.R.4
Minnaard, A.J.5
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122
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3843127786
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b) F. Spindler, C. Malan, M. Lotz, M. Kesselgruber, U. Pittelkow, A. Rivas-Nass, O. Briel, H.-U. Blaser, Tetrahedron: Asymmetry 2004, 15, 2299.
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Tetrahedron: Asymmetry
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Spindler, F.1
Malan, C.2
Lotz, M.3
Kesselgruber, M.4
Pittelkow, U.5
Rivas-Nass, A.6
Briel, O.7
Blaser, H.-U.8
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124
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33746186939
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note
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[34a]
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