## Abstract Azomethine ylides generated from 5‐(alkoxycarbonylmethyl)phenanthridinium cations were studied in 1,3‐dipolar cycloadditions with dimethyl maleate and dimethyl fumarate as dipolarophiles. The cycloadducts with the pyrrolidino[1,2‐f]phenanthridine skeleton easily underwent dehydrogenatio
Diastereofacial selectivity in the 1,3-dipolar cycloaddition of chiral azomethine ylides
✍ Scribed by Pierre Deprez; Jacques Rouden; Angèle Chiaroni; Claude Riche; Jacques Royer; Henri-Philippe Husson
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 247 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
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
Methods are described of synthesizing various 3-carboxy-4-vinyl pyrrolidines, versatile building blocks for our drug discovery efforts. The 1,3-dipolar cycloaddition between activated olefins and nonstabilized azomethine ylide is a known method for synthesizing pyrrolidines in a stereospecific manne