Direct catalytic diastereoselective Mannich reactions: the synthesis of protected α-hydroxy-β-aminoketones |
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Authors: | Nikki E. Stainforth Gary A. Cutting Matthew P. John Michael C. Willis |
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Affiliation: | 1. Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK;2. Department of Chemistry, University of Bath, Bath BA2 7AY, UK;3. Chemical Development Division, GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage SG1 2NY, UK |
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Abstract: | The combination of Mg(ClO4)2, 2,2′-bipyridine and N-methylmorpholine generates an effective catalyst system for the direct addition of α-carbonate-substituted ketones to aryl N-Ts imines. Methyl-carbonate-substituted ketones deliver acyclic α-hydroxy-β-aminoketone derivates, while ketones substituted with α-iso-propenyl-carbonates furnish cyclic carbamate adducts. In both cases the anti-configured Mannich products dominate. |
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