Stereoselective ketene-claisen rearrangement of chiral allylthioethers
✍ Scribed by Reinhold Oehrlein; Rainer Jeschke; Beat Ernst; Daniel Bellus
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 248 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
A synthetic route for crownophanes containing a chiral binaphthyl unit using tandem Claisen rearrangement is described to demonstrate the versatility of this approach. Molecular recognition by the resulting crownophane for butylurea is also investigated.
## Abstract Allenic silyl ketene acetals 3 formed by conjugate 1,6‐addition of organocuprates to 2‐propen‐1‐yl and 2‐buten‐1‐yl 2‐en‐4‐ynoates 1 and regioselective enolate capture with silyl electrophiles readily undergo [3,3]‐Ireland‐Claisen rearrangements to the 2‐substituted methyl 3,4‐dienoates
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