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.
✦ LIBER ✦
[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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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