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It should be noted that 6 and 6′ are less effective catalysts compared to 8, giving the catalytic product in very low yield. In the solid state a p-nitrophenolate counterion in catalyst 6 was found to be in a different position with respect to the quaternary nitrogen atom, compared to the same counterion in catalyst 8, presumably due to the steric effects exerted by the 1-adamantoyl substituent. For a discussion, see ref 21i
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It should be noted that 6 and 6′ are less effective catalysts compared to 8, giving the catalytic product in very low yield. In the solid state a p-nitrophenolate counterion in catalyst 6 was found to be in a different position with respect to the quaternary nitrogen atom, compared to the same counterion in catalyst 8, presumably due to the steric effects exerted by the 1-adamantoyl substituent. For a discussion, see ref 21i.
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It has to be noted that the more bulky glycine imine 2b has an opposite effect on the enantioselectivity with catalyst 8 giving the product 5b with only 35% ee.
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It has to be noted that the more bulky glycine imine 2b has an opposite effect on the enantioselectivity with catalyst 8 giving the product 5b with only 35% ee.
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