Highly enantioselective synthesis of rigid, quaternary 1,4-benzodiazepine-2,5-diones derived from proline |
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Authors: | MacQuarrie-Hunter Stephanie Carlier Paul R |
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Affiliation: | Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, USA. |
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Abstract: | [reaction: see text] Proline-derived 1,4-benzodiazepine-2,5-diones are extremely useful scaffolds in medicinal chemistry. In this paper, we describe a protocol for retentive C3 alkylation of these materials, thus accomplishing the direct synthesis of enantiopure quaternary 1,4-benzodiazepine-2,5-diones. The high enantioselectivities (up to 99.5%) are attributed to memory of chirality. |
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