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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