Asymmetric syntheses. Part 11. Reduction of ketones and related ketone oximes with lithium aluminium hydride–3-O-cyclohexylmethyl-1,2-O-cyclohexylidene-α-D-glucofuranose complex to give optically active alcohols and amines
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 493-496
- https://doi.org/10.1039/p19840000493
Abstract
The asymmetric reduction of ketones and structurally related isoelectronic ketone oximes with lithium aluminium hydride–3-O-cyclohexylmethyl-1,2-O-cyclohexylidene-α-D-glucofuranose complex yields optically active alcohols of up to 42% optical purity and optically active amines of up to 52% optical purity, respectively. The resulting alcohols as well as amines all have the S-configuration. When the asymmetric reduction is carried out with the ethanol-modified glucofuranose complex, the resulting alcohols and amines have the R-configuration.Keywords
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