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Catalytic and asymmetric [2,3]sigmatropic rearrangement: Co(III)-salen catalyzed S-ylide formation from allyl aryl sulfides and their rearrangement

✍ Scribed by Tsutomu Fukuda; Ryo Irie; Tsutomu Katsuki

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
998 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

Reaction of allyl aryl sulfides and a-diazoacetic acid esters in the presence of optically active Co(HD-salen complex (8-Br) provided 3-substituted 2-arylthio-4-pentenoic acid esters stereo~l~vely by way of enantioselcctive S-ylide formation and subse~luent diastereoselective [2,3]sismalropic rearrangement. For example, the reaction of Β’innamyl phenyl sulfide and (-)-menthyl a-diazoacctatc provided (-)-manthyl (2R,3~-2-phenylthio-3-phenyl-4-pentanoate of 74% de prefereutially.

πŸ“œ SIMILAR VOLUMES

Co(III)-salen catalyzed carbenoid reacti
Co(III)-salen catalyzed carbenoid reaction: Stereoselective [2,3]sigmatropic rearrangement of S-ylides derived from allyl aryl sulfides
✍ Tsutomu Fukuda; Tsutomu Katsuki πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 224 KB

Allyi aryl sulfides and diazoacetic acid esters react in the presence of optically active Co(lll)salen complex (4) with good enantioselectivity, to give the [2,31sigmatropic rearrangement products, 2arylthio-3-aryl-4-pentenoic acid esters, via the corresponding S-ylides.

Metal-catalyzed ylide formation and [2,3
Metal-catalyzed ylide formation and [2,3] sigmatropic rearrangement of allyl sulfides with trimethylsilyldiazomethane
✍ David S. Carter; David L. Van Vranken πŸ“‚ Article πŸ“… 1999 πŸ› Elsevier Science 🌐 French βš– 230 KB

Trimethylsilyldiazomethane is compared with ethyl diazoacetate for the rhodium, copper, and cobalt catalyzed formation and [2,3] rearrangement of allylsulfonium ylides. At room temperature, the reaction can be carried out using the allyl sulfide as the limiting reagent by slow addition of 3 equivale