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Aldimine
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We have already found that lanthanide triflates are effective catalysts for the reactions of aldehydes or aldimines with silyl enol ethers or ketene silyl acetals. (a) Aldehyde: Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625. (b) Aldimine: Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. See, also: (c) Kobayashi, S.; Hachiya, I.; Suzuki, S.; Moriwaki, M. Tetrahedron Lett. 1996, 37, 2809.
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We have already found that lanthanide triflates are effective catalysts for the reactions of aldehydes or aldimines with silyl enol ethers or ketene silyl acetals. (a) Aldehyde: Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625. (b) Aldimine: Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233. See, also: (c) Kobayashi, S.; Hachiya, I.; Suzuki, S.; Moriwaki, M. Tetrahedron Lett. 1996, 37, 2809.
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It is noted that the yields are much improved compared to those shown in ref 16b
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It is noted that the yields are much improved compared to those shown in ref 16b.
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23 We have several contrary experimental results concerning this proposal, and the present paper is thought to be one of them. Precise discussion will be reported in due course. In addition, these results may open a door to develop chiral Lewis acid catalysis in enantioselective reactions of aldimines with silylated nucleophiles, which is one of the most difficult and challenging themes. Cf.: Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153.
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