Optically active enantiomers of substituted glyceraldehydes or glycidaldehydes formed as subtituted 1,5- dihydro-3H-2,4-benzodioxepines
US5162554A · kind A · utility
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Key dates
| Filing date | Jun 18, 1991 |
| Grant date | Nov 10, 1992 |
| Priority date | — |
| Expiry date | Jun 18, 2011 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D411/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Stable, optically active enantiomers of substituted glyceraldehydes or glycidaldehydes are synthesized by using osmium-catalyzed asymmetric dihydroxylation of an olefin which is a substituted 1,5-dihydro-3H-2,4-benzodioxepine. For example, the protected glyceraldehyde, 3-(1,2-dihydroxyethyl)-1,5-dihydro-3H-2,4-benzodioxepine and the protected glycidaldehyde, 3-(1,2-epoxyethyl)-1,5-dihydro-3H-2,4-benzodioxepine have been synthesized and the optical enantiomer has been recovered. In the synthetic and isolation methods, enantiomers with high enantiomeric excess are recovered from the mother liquor following a recrystallization step.
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