Palladium-catalyzed decarboxylation-allylation of allylic esters of. alpha.-substituted. beta.-keto carboxylic, malonic, cyanoacetic, and nitroacetic acids
J Tsuji, T Yamada, I Minami, M Yuhara…
Index: Tsuji, Jiro,; Yamada, Toshiro; Minami, Ichiro; Yuhara, Masami; Nisar, Mohammad; Shimizu, Isao Journal of Organic Chemistry, 1987 , vol. 52, # 14 p. 2988 - 2995
Full Text: HTML
Citation Number: 116
Abstract
Decarboxylation-allylation of allylic P-keto carboxylates using P~(OAC)~--PP~~ or Pd2 (dba) 3CHC1,-dppe as a catalyst proceeds smoothly to give a-allylated ketones. The reaction is highly regioselective. In some cases, diallylated ketones are obtained with allylic esters bearing an active proton (s). Also rhodium, molybdenum, and nickel complexes are active catalysts in this reaction. Similarly allylic esters of a-substituted malonates, cyanoacetates, ...
Related Articles:
Allylation of active methylene compounds with allyl oxime carbonates catalyzed by Pd (0)
[Suzuki, Osamu; Hashiguchi, Yoshiharu; Inoue, Seiichi; Sato, Kikumasa Chemistry Letters, 1988 , p. 291 - 294]
Epoxides from myrcene: New versatile tools for the synthesis of functionalized acyclic terpenoids
[Fauchet; Miguel, B. Arreguy-San; Taran; Delmond Synthetic Communications, 1999 , vol. 29, # 21 p. 3673 - 3684]
[Arterburn, Jeffrey B.; Liu, Minghua; Perry, Marc C. Helvetica Chimica Acta, 2002 , vol. 85, # 10 p. 3225 - 3236]
[Fujiwara, Tooru; Iwasaki, Toshiaki; Takeda, Takeshi Chemistry Letters, 1993 , # 8 p. 1321 - 1324]
The ester enolate Carroll rearrangement
[Wilson , Stephen R.; Price, Martyn F. Journal of Organic Chemistry, 1984 , vol. 49, # 4 p. 722 - 725]