The reaction of (E)-2-phenyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-ylmethylen]-5(4H)-oxazolone with diazomethane has been studied under a variety of reaction conditions, and the results compared with those obtained with the corresponding (Z)-isomer. The origin of the high diastereofacial selectivity in
1,3-Dipolar cycloaddition of diazomethane with a chiral azlactone
✍ Scribed by Carlos Cativiela; María D Díaz-de-Villegas; Ana I Jiménez; Fernando Lahoz
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 314 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The chiral Z-azlactone derived from 1.2-0-isopropylidene-D-glyceraldehyde reacted with diazomethane to amrd stereoseiectively and diastereoselectively a cis Spiro-azlactone.
Solvent and temperature &per&nce of the ratio of the producti is described e$-Didehydtoamino acid derivatives ate useful pmchiral building blocks in synthetic organic chemisuy. In
📜 SIMILAR VOLUMES
Perturbational molecular orbital methods have furnished a clue to the problems of reactivity and regioselectivity in 1,34polar cycloadditions. 1 Within the framework of frontier molecular orbital theory 2 semiquantitative correlations of mte data with orbital energy sepamtions were obtained. In orde
## Abstract For Abstract see ChemInform Abstract in Full Text.
## Abstract Novel 2‐pyrazolines were obtained by the cycloaddition of diazomethane to bis(arylsulfonylethenyl)‐sulfones (**3**) and 1‐arylsulfonyl‐2‐styrylsulfonylethenes (7). Dehydrogenation of 2‐pyrazolines with chloranil gave pyrazoles.