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and references therein. For metal-catalyzed asymmetric conjugate amine addition to enones, see: a
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The results obtained by using the catalyst combination 1a or 9-amino(9-deoxy)epi-hydroquinine 2 in combination with different counteranions (trifluoroacetate, tosylate, benzoate) in the organocatalyzed aziridination did not bring any appreciable improvement in chemo- or stereoselectivity, confirming the superior efficiency of the catalyst salt 1b. Using the opposite enantiomeric counteranion 3 (L-N-Boc phenylglycine) afforded the same enantiomeric products 10 with lower reactivity and selectivity.
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The results obtained by using the catalyst combination 1a or 9-amino(9-deoxy)epi-hydroquinine 2 in combination with different counteranions (trifluoroacetate, tosylate, benzoate) in the organocatalyzed aziridination did not bring any appreciable improvement in chemo- or stereoselectivity, confirming the superior efficiency of the catalyst salt 1b. Using the opposite enantiomeric counteranion 3 (L-N-Boc phenylglycine) afforded the same enantiomeric products 10 with lower reactivity and selectivity.
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46
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43249111803
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For the use of a similar catalytic system in the highly enantioselective epoxidation of cyclic enones, see: a X. Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2008, 130, 6070
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