In the presence of a cinchona alkaloid as a catalyst, the Diels-Alder reaction of 3-hydroxy-2-pyrone with chiral N-acryloyl oxazolidinone afforded a bicyclolactone adduct with high diastereoselectivities (up to 95%de) in almost quantitative yield.
Asymmetric Diels—Alder Reactions of 2-Pyrones with a Bifunctional Organic Catalyst.
✍ Scribed by Yi Wang; Hongming Li; Yong-Qiang Wang; Yan Liu; Bruce M. Foxman; Li Deng
- Publisher
- John Wiley and Sons
- Year
- 2007
- Weight
- 43 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0931-7597
No coin nor oath required. For personal study only.
📜 SIMILAR VOLUMES
The aza-Diels-Alder reaction of substituted indole 2-carboxaldehydes with Danishefsky's diene has been investigated. The reaction proceeds with a high degree of diastereoselectivity providing highly functionalized 2-(2-piperidyl)indoles which are further elaborated into novel polycyclic heterocycles
## Abstract For Abstract see ChemInform Abstract in Full Text.
The Diels-Alder reaction of 4-aryl-pyrones with electron-rich dienophiles afforded substituted biaryl derivatives in most cases. At the minimal temperatures necessary for a measurable conversion of the starting pyrones, the bicyclic lactones, the primary products of the condensation, underwent cyclo