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Macrocyclic oxonium ylide formation and internal [2,3]-sigmatropic rearrangement. Catalyst influence on selectivity

โœ 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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โœฆ 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.


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Enantioselective [2,3]-sigmatropic and [
โœ Shinji Kitagaki; Yoshimasa Yanamoto; Hideyuki Tsutsui; Masahiro Anada; Makoto Na ๐Ÿ“‚ Article ๐Ÿ“… 2001 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 79 KB

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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