The preparation of a variety of highly substituted pyrrolidines was achieved by solid-phase synthesis through the [2rts + 4~s] cycloaddition of 2-azaallyl anions with alkenes. Resin-bound aldehydes 2 were condensed with ct-arnino stannanes 3 to afford (2-azaallyl)stannanes 4. Transmetalation of 4 wi
Intramolecular 2-azaallyl anion cycloadditions. Application to the synthesis of fused bicyclic pyrrolidines
β Scribed by Pearson, William H.; Walters, Michael A.; Oswell, Kira D.
- Book ID
- 126047345
- Publisher
- American Chemical Society
- Year
- 1986
- Tongue
- English
- Weight
- 376 KB
- Volume
- 108
- Category
- Article
- ISSN
- 0002-7863
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π SIMILAR VOLUMES
A highly functionalized perhydroindole is formed by the intramolecular [Ο4s+Ο2s] cycloaddition of a 2-azaallyl anion with a vinyl sulfide [Eq. (a)]. This is the key step in the total synthesis of (+)-coccinine, the enantiomer of the Amaryllidaceae alkaloid (-)-coccinine.
Application of the 2-Azaallyl Anion Cycloaddition Method to an Enantioselective Total Synthesis of (+)-Coccinine. -The nonnatural enantiomer (XI) of the alkaloid (-)-coccinine is enantioselectively synthesized with cycloaddition of (VII) to (VIII) as the key step. -(PEARSON, W. H.;