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j) R. O. Duthaler, A. Hafner, Angew. Chem. 1997, 109, 43; Angew. Chem. Int. Ed. Engl. 1997, 36, 43; notable examples of chiral Lewis basecatalyzed asymmetric allylations with allylic trichlorosilanes;
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25
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0029895814
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The BINAP + AgOTf complex was shown to be a good chiral catalyst for asymmetric allylation of aldehydes with allylic trialkyltin compounds: A. Yanagisawa, H. Nakashima, A. Ishiba, H. Yamamoto, J. Am. Chem. Soc. 1996, 118, 4723.
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b) E. Nakamura, M. Shimizu, I. Kuwajima, J. Sakata, K. Yokoyama, R. Noyori, J. Org. Chem. 1983, 48, 932.
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28
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0342612986
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-
note
-
1H NMR spectroscopy, and a 0.6/1 mixture was found to give the desired 1:1 complex without significant formation of the 2:1 complex.
-
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29
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0011404010
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H. Takaya, K. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, R. Noyori, J. Org. Chem. 1986, 51, 629 . (R)-and (S)-p-Tol-BINAP are commercially available (AZmax).
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Noyori, R.8
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30
-
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0343918733
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-
Aliphatic aldehydes were unreactive under the standard reaction conditions. For example, the reaction with hydrocinnamaldehyde at - 20 C for 30 min and then at room temperature for 8 h gave the allylated product in only 3% yield and with 85% ee
-
Aliphatic aldehydes were unreactive under the standard reaction conditions. For example, the reaction with hydrocinnamaldehyde at - 20 C for 30 min and then at room temperature for 8 h gave the allylated product in only 3% yield and with 85% ee.
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32
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0001525348
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b) R. W. Hoffmann, Angew. Chem. 1982, 94, 569; Angew. Chem. Int. Ed. Engl. 1982, 21, 555.
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A. Yanagisawa, A. Ishiba, H. Nakashima, H. Yamamoto, Synlett 1997, 88.
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Yanagisawa, A.1
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35
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0343918731
-
-
note
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3SiF. The formation of this compound is an indication for a crotylsilver species. Signals assignable to the crotylsilver or hydrolyzed butenes were not observed.
-
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37
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0000703343
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0001671926
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a) M. Riediker, R. O. Duthaler, Angew. Chem. 1989, 101, 488; Angew. Chem. Int. Ed. Engl. 1989, 28, 494;
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42
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0004600164
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For another method of preparation of the racemic compound, see a) C. Chen, Y. Shen, Y.-Z. Huang, Tetrahedron Lett. 1988, 29, 1395; for a method of analytical resolution of the racemic compound, see
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Chen, C.1
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