Synthesis of 5-Aryloxazolidines via 1,3-Dipolar Cycloaddition Reaction of a Non-Stabilized Azomethine Ylide with Aromatic Aldehydes
β Scribed by Ryan, John H.; Spiccia, Nadia; Wong, Leon S.-M.; Holmes, Andrew B.
- Book ID
- 118016499
- Publisher
- Commonwealth Scientific and Industrial Research Organisation Publishing
- Year
- 2007
- Tongue
- English
- Weight
- 282 KB
- Volume
- 60
- Category
- Article
- ISSN
- 0004-9425
- DOI
- 10.1071/ch07282
No coin nor oath required. For personal study only.
π SIMILAR VOLUMES
Substituted 1-oxapyrrolizidines have been synthetized by cycloaddition of azomethi?e ylides, generated by aldehydes induced decarboxylation of proline, with dipolarophylei.' The carbonyl stbreochernistry of the cycloadducts indicate that they arise from the stereospecific formation of one is6mer of
1,3-Dipolar cycloaddition of D-glucose-derived azomethine ylides for the synthesis of chiral pyrrolidines accompanied an unexpected 1,2-elimination in the furanose moiety of the products. The C3 0 alkoxy/ hydroxy group of the furanose moiety was invariably eliminated under the reaction conditions. A