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Recyclable supported chiral amines for use within highly efficient asymmetric Mg-amide base processes

Kerr, William J. and Pazicky, Marek and McArthur, Duncan. (2008) Recyclable supported chiral amines for use within highly efficient asymmetric Mg-amide base processes. In: Asymmetric Reactions and Syntheses, 2008-08-17.

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In 2000, our group reported on the first examples of successful deprotonations of 4-substituted cyclohexanones, using simple magnesium amide base chem., with the com. available chiral amine (R)-(+)-N-benzyl-a-methylbenzylamine. Further applications to asym. deprotonation reactions with alternative chiral base species have now been developed. In particular, new supported C2-sym. magnesium amide bases have been established. In turn, novel sol. and insol. polymers have been applied to the asym. deprotonation reaction of prochiral ketones with superb selectivity (Scheme 1). Furthermore, a supported base recycling protocol has also been developed. [on SciFinder(R)]