Competitive [2,3]- and [1,2]-Oxonium Ylide Rearrangements. Concerted or Stepwise?
โ Scribed by Jaber, Deana M.; Burgin, Ryan N.; Helper, Matthew; Zavalij, Peter Y.; Doyle, Michael P.
- Book ID
- 126323634
- Publisher
- American Chemical Society
- Year
- 2012
- Tongue
- English
- Weight
- 515 KB
- Volume
- 14
- Category
- Article
- ISSN
- 1523-7060
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๐ SIMILAR VOLUMES
The formation of 13-membered ring oxonium ylides and their subsequent stereocontrolled [2,3]-sigmatropic rearrangement to l O-membered ring lactones occurs in catalyst dependent competition with macrocyfic cyclopropanation.
Tandem intramolecular generation and rearrangement of allylic oxonium ylides from a-diazo b-keto esters has been effected with the aid of dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] in toluene, providing benzofuran-3-ones via [2,3]-sigmatropic rearrangement in up to 76% ee. In systems wit
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