Macrocyclic oxonium ylide formation and internal [2,3]-sigmatropic rearrangement. Catalyst influence on selectivity
โ Scribed by Michael P. Doyle; Chad S. Peterson
- Book ID
- 104257516
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 198 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
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.
๐ SIMILAR VOLUMES
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
In this paper, the authors describe the tandem oxonium ylide formation and [2,3]-sigmatropic rearrangement from 1b using Rh 2 (R-DDBNP) 4 (up to 62% ee).