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The remarkable effect of the 7-substituent in the diastereoselective oxidative rearrangement of indoles: Asymmetric synthesis of 3,3-disubstituted oxindoles

✍ Scribed by Lachia, Mathilde ;Poriel, Cyril ;Slawin, Alexandra M. Z. ;Moody, Christopher J.


Book ID
120499160
Publisher
Royal Society of Chemistry
Year
2007
Tongue
English
Weight
251 KB
Volume
3
Category
Article
ISSN
1359-7345

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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