Synthesis of Hydroxyalkyl Heterocycles by Ring Transformation of Spiroepoxy Lactones with Binucleophiles.
β Scribed by Andreas Otto; Juergen Liebscher
- Publisher
- John Wiley and Sons
- Year
- 2003
- Weight
- 156 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0931-7597
No coin nor oath required. For personal study only.
π SIMILAR VOLUMES
Enantiopure Ξ±-alkylidenelactones 7 were prepared by a Michael-like addition and ring-chain transformation affording optically active 4-(Ο-hydroxyalkyl)pyrazolidin-3-Wittig reaction from Ξ±-bromolactones 4 and chiral aldehydes 6. Compounds 7 react with hydrazines 9 by stereoselective ones 11.
The configuration and/or formulae of the following compounds need to be corrected. (1ΠR,E)-3-(2-Benzyloxy-3-hydroxypropylidene)dihydrofuran-2-one (7c): Correct formula: (4S,5R,4ΠS)-5-(2,2-Dimethyl[1,3]dioxolan-4-yl)-4-(2-hydroxyethyl)pyrazolidin-3-one (11a): Original formula correct (4R,5S,1ΠR)-5-(1
## Abstract For Abstract see ChemInform Abstract in Full Text.
Synthesis of Chiral 4-(Ο-Hydroxyalkyl)pyrazolidin-3-ones by Ring-Chain Transformation of Ξ±-Alkylidenelactones with Hydrazines. -This is the first access to optically active 4-(Ο-hydroxyalkyl)pyrazolidin-3-ones. The lactone (IX), however, cannot be transformed into the corresponding pyrazolidinone.