105142-12-9Relevant articles and documents
Dication Ethers, 11. - Ambidoselective Reactions of β-Ketoenolates with Dication Ethers
Feith, Bernhard,Weber, Hans-Martin,Maas, Gerhard
, p. 2123 - 2141 (2007/10/02)
When the bis(N,N,N',N'-tetramethylformamidinio) ether salt 5a is treated with the β-ketoenolates 7a-h, j or β-ketonitrile anion 7i in acetonitrile, electrophilic transfer of a tetramethylformamidino group occurs exclusively at an oxygen atom of the ambident anions, thus yielding uronium salts 8a-j.From the acyclic β-ketoenolates 7a-f, β-acylenol ether salts (E)-8a-f are obtained diastereoselectively.Also, electrophilic attack by the diimidazolinio ether salt 5b and the dipyridino ether salt 5c,d occurs exclusively at an oxygen atom of the dimedone anion (8k, 15, 18).From 5c and the anion of Meldrum's acid, olefin 16 is formed by C/C bond connection. - An X-ray structure analysis of (E)-8f was performed.