ChemInform Abstract: Oxygen-Directed Carbocyclizations of 2,3-Epoxy Alcohols: Stereoselective Construction of Polyfunctionalized Seven-Membered Rings by 7-endo-Tet Ring Closures.
✍ Scribed by Charles M. Marson; Jane McGregor; Afzal Khan; Trevor J. Grinter
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 36 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Oxygen-Directed Carbocyclizations of 2,3-Epoxy Alcohols: Stereoselective Construction of Polyfunctionalized Seven-Membered Rings by 7-endo-Tet Ring Closures. -The first examples of alkyne-epoxy alcohol cyclizations that lead to seven-membered carbocyclic rings are reported together with the first comprehensive study that demarcates the influence of bidentate chelation control during cyclizations of 2,3-epoxy alcohols. An alkyne or alkene terminus is shown to cyclize onto an epoxy alcohol unit to give a cycloheptanoid ring incorporating syn-1,2-dihydroxylated functionality.
Unusually, these carbocyclizations take place at the less substituted epoxide carbon atom of the epoxy alcohols. -(MARSON,