Diastereoselective addition of HCN to Garner's aldehyde |
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| Affiliation: | 1. Department of Biomolecular Systems, Max-Planck Institute of Colloids and Interfaces, Potsdam, Germany;2. Department of Chemistry and Chemical Engineering, Chalmers University of Technology, Göteborg, Sweden |
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| Abstract: | The hydrocyanation of N-Boc-N,O-isopropylidene-l-serinal 1 (Garner's aldehyde) is described. The influence of various reaction conditions (solvent, temperature, addition of a Lewis acid, presence of a biocatalyst) on the stereochemical outcome of the addition of HCN was investigated. The use of 2-pentanol as the solvent at room temperature afforded complete stereoselectivity. X-Ray analysis of the product showed the anti configuration. The results can be readily explained on the basis of a Felkin–Anh type model. |
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