Stereospecific synthesis of 5-substituted 1,3-dioxanes by application of dimroth's principle
β Scribed by J.C. Jochims; Y. Kobayashi
- Publisher
- Elsevier Science
- Year
- 1974
- Tongue
- French
- Weight
- 168 KB
- Volume
- 15
- Category
- Article
- ISSN
- 0040-4039
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The title compound is prepared in 78% yield using an improved one-pot procedure which does not require final purification. The title compound (4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-amine ( 1) is an effective reagent for the synthesis of optically active amino acids (2)l and d-methyl amino acids
## Abstract (2__R__,4__S__,5__S__)β(+)β5β(2,2βDichloroacetamido)β4β(4βnitrophenyl)β2βarylβ1,3βdioxanes **3β8** were synthesized with high diastereoselectivity and good yields. The structures of acetals were determined and the configurations were confirmed by 2DβNMR (NOESY) and Xβray crystallographi
Epoxidation of the 5-ylidene-l,3-dioxane-4-ones 3 with dimethyldioxirane (4) affords enantiomerically pure oxiranes 5 in satisfactory yields. These products 5 are novel hydroxyethyloxiranecarboxylic acid derivatives and can be reduced to enantiomericaily pure 5 -(ot-hydroxyalkyl)-1,3 -dioxane-4-ones