Stereocontrolled one-pot conversions of α-alkoxy esters to syn- and anti-1,2-diol derivatives
✍ Scribed by Steven D. Burke; David N. Deaton; Robert J. Olsen; David M. Armistead; Bruce E. Blough
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 155 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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A new route to enantiopure syn and anti 1,2-diols is described from oxalyl-di-(Nmethyl-N-methoxyamide) via the corresponding ~-ketosulfoxide. This is the first report of the stereoselective reduction ofaT--keto-~-hydroxysulfoxide.
The asymmetric hydrogenation of methyl 3,5-syn-2 in up to 92% de but with poor enantiomeric excesses. In all cases, methyl (R)-3-hydroxy-5-oxohexanoate [(R)-11] is dioxohexanoate (1) into mixtures of 3,5-dihydroxyesters (2) and 3-hydroxylactones (3) has been reinvestigated with a the exclusive prima