1,3-Dipolar cycloadditions of azomethine ylides with dipolarophiles. II. Synthesis of pyrrolizidines
✍ Scribed by F. Orsini; F. Pelizzoni; M. Forte; M. Sisti; F. Merati; P. Gariboldi
- Book ID
- 112129102
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1988
- Tongue
- English
- Weight
- 487 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0022-152X
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## 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
## Abstract The 1,3‐dipolar cycloaddition reactions of chiral five‐membered cyclic azomethine ylides, generated in situ from ethyl glyoxylate and protected (3__S__,4__S__)‐dihydroxypyrrolidines **3** and **6** have been studied. The facial selectivity of the cycloaddition reaction is governed by th