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[2,3]-Wittig rearrangement of allylic glycolate esters via boron and tin enolates

✍ Scribed by Taeboem Oh; Zbigniew Wrobel; Steven M. Rubenstein


Book ID
108381915
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
249 KB
Volume
32
Category
Article
ISSN
0040-4039

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Asymmetric Induction and Simple Diastere
✍ BrΓΌckner, Reinhard πŸ“‚ Article πŸ“… 1989 πŸ› Wiley (John Wiley & Sons) 🌐 English βš– 860 KB

The [2,3] Wittig rearrangements of the lithio enolates of the cisconfigurated allylic ethers 5a -d are stereoselective. The tert-butyl ester 5d gives 79% of a single rearrangement product 6d. The chiral center of the dioxolane controls the configuration at one of the newly formed stereogenic centers