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3643097108
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note
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Some of the TMS ethers resulting from condensation are hydrolytically unstable. For these products, the standard workup procedures involving exposure of the crude products to dilute acid resulted in removal of the TMS ether.
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10
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3643061685
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note
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In a control experiment, treatment of hexanal with TBAT under the described conditions in the absence of allyltrimethylsilane did not produce aldol products.
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13
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14
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0001226919
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(d) Sakurai has also reported the fluoride-catalyzed condensation of crotyltrifluorosilane derivatives with aldehydes: Kira, M.; Kobayashi, M.; Sakurai, H. Tetrahedron Lett. 1987, 28, 4081. (e) Sakurai, H. Synlett 1990, 1 and references cited therein.
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0001226919
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(d) Sakurai has also reported the fluoride-catalyzed condensation of crotyltrifluorosilane derivatives with aldehydes: Kira, M.; Kobayashi, M.; Sakurai, H. Tetrahedron Lett. 1987, 28, 4081. (e) Sakurai, H. Synlett 1990, 1 and references cited therein.
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Sakurai, H.1
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84972899517
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This is the first example of fluoride-initiated intermolecular coupling between allyltrimethylsilane and an imine derivative. For an example of an alkoxide-induced reaction between an imine and a benzylsilane derivative, see: Shimizu, S.; Ogata, M. Synth.Commun. 1989, 19, 2219.
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For an account of the reaction between imines and allenyl silanes, see: Jin, J.; Smith, D. T.; Weinreb, S. M. J. Org. Chem. 1995, 60, 5366. Borzilleri, R. M.; Weinreb, S. M.; Parzez, M. J. Am Chem. Soc. 1994, 116, 9789.
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For an account of the reaction between imines and allenyl silanes, see: Jin, J.; Smith, D. T.; Weinreb, S. M. J. Org. Chem. 1995, 60, 5366. Borzilleri, R. M.; Weinreb, S. M.; Parzez, M. J. Am Chem. Soc. 1994, 116, 9789.
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Unpublished results
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Unpublished results, A. S. Pilcher, P. Loeszos, J. W. Schwantes, V. Lee, and A. L. Slover.
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Pilcher, A.S.1
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