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37049099843
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For recent examples of truly catalytic (catalyst loading <10 mol %) nucleophilic substitution reactions of N-acyliminium ion precursors using TMSOTf see: (a) Barrett, A. G. M.; Quayle, P. J. Chem. Soc., Chem. Commun. 1981, 1076.
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0033944318
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Recently, Kobayashi and co-workers reported efficient nucleophilic substitution reactions of methoxy and acetoxy N-carbonyl piperidine derivatives by trialkylsilyl nucleophiles catalyzed by 10 mol % of various metal triflates: (a) Okitsu, O.; Suzuki, R.; Kobayashi, S. Synlett 2000, 989.
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25
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28244434016
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see refs 1a, 2a, 4, 5, and 6
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2 have been claimed to be formed in situ, see refs 1a, 2a, 4, 5, and 6.
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0030069493
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Louwrier, S.; Ostendorf, M.; Boom, A.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1996, 52, 2603.
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note
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Such applications have been fully realized in our lab and will be published soon.
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28244469544
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see ref 8a
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The alkylations examined herein afforded comparable stereoselectivities as those catalyzed by TIPSOTf or promoted by conventional Lewis acids; see ref 8a.
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