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[2,3]Wittig rearrangement of 2′-alkenyloxyacetic acid esters

✍ Scribed by Masako Uchikawa; Tsutomu Katsuki; Masaru Yamaguchi


Book ID
104219088
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
118 KB
Volume
27
Category
Article
ISSN
0040-4039

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Stereoelectronically controlled [2,3]wit
✍ Akira Ishikawa; Harumi Uchiyama; Tsutomu Katsuki; Masaru Yamaguchi 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 208 KB

2,31Wittig rearrangement of 2'-heterosubstituted alkenyloxyacetic acid esters exhibited anti,Z-selectivity, which can be attributed to the interaction between the -nonbonding orbital on the ether oxygen atom and the anti-bonding orbital of carbonheteroatom bond.

The ester dienolate [2,3]-Wittig rearran
✍ Martin Hiersemann 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 928 KB

The ester dienolate [2,3]-Wittig rearrangement proceeds with high yield and anti/syn diastereoselection to afford 3-alkoxycarbonyl-3-hydroxy-substituted 1,5-hexadienes. No donor solvent or metal salt additive was necessary to trigger the rearrangement. The rearrangement product was transformed to di