Atropo-enantioselective reduction of configurationally unstable biaryl lactones with BINAL-H |
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Institution: | 1. University of Padua Medical School, Department of Cardiologic, Thoracic and Vascular Sciences, Padua, Italy;2. University of Padua Medical School, Department of Medicine, Thrombohemorrhagic Disorders Unit, Padua, Italy |
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Abstract: | The atropo-enantioselective reduction of configurationally unstable biaryl lactones with BINAL-H yields axially chiral biaryl alcohols in high enantiomeric ratios of up to 94:6 (er >99.5:0.5 after one crystallization step). Within this two-step reduction process the stereochemically deciding step is the first attack on the lactones and not the reduction of the likewise configurationally unstable biaryl lactol/hydroxy aldehyde intermediates, as evident from the non-stereoselective reduction of the latter under the same conditions. |
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