Highly Diastereoselective Synthesis of 2,6-Di[1-(2-alkylaziridin-1-yl)alkyl]pyridines, Useful Ligands in Palladium-Catalyzed Asymmetric Allylic Alkylation
✍ Scribed by Diego Savoia; Giuseppe Alvaro; Romano Di Fabio; Claudio Fiorelli; Andrea Gualandi; Magda Monari; Fabio Piccinelli
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 238 KB
- Volume
- 348
- Category
- Article
- ISSN
- 1615-4150
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✦ Synopsis
Abstract
C~2~‐Symmetrical, enantiopure 2,6‐di[1‐(1‐aziridinyl)alkyl]pyridines (DIAZAPs) were prepared by a high‐yielding, three‐step sequence starting from 2,6‐pyridinedicarbaldehyde and (S)‐valinol or (S)‐phenylglycinol. The new compounds were tested as ligands in palladium‐catalyzed allylation of carbanions in different solvents. Almost quantitative yield and up to 99 % enantiomeric excess were obtained in the reactions of the enolates derived from malonate, phenyl‐ and benzylmalonate dimethyl esters with 1,3‐diphenyl‐2‐propenyl ethyl carbonate.