85028-48-4Relevant academic research and scientific papers
Novel one-pot synthesis of N-alkyl arylamines from oxime ethers using organometallic reagents
Mukhopadhyay, Partha P.,Miyata, Okiko,Naito, Takeaki
, p. 1403 - 1406 (2008/02/13)
A novel one-pot synthesis of α,α-disubstituted secondary arylamines from oxime ethers has been developed by two separate additions of organometallic reagents. As a related arylamine construction, very efficient synthesis of N-(diallyl)methyl arylamines is
Novel and efficient method for the allylation of carbonyl compounds and imines using triallylaluminum
Shen, Kao-Hsien,Yao, Ching-Fa
, p. 3980 - 3983 (2007/10/03)
This is the first report of the use of triallylaluminum as a reagent for the allylation of carbonyl compounds and imines. The allylation of ketimines without additional metal catalyst is known so far only in the case of the Grignard reagent. Triallylaluminum is a useful alternative to provide the homoallylic amines in excellent yield upon addition to aldimines and ketimines. The significant reactivity of this reagent was confirmed by its reaction with a sterically rigid ketone such as adamantanone to provide 1-adamantyl-3-buten-1-ol in 98% yield. The chemoselectivity of triallyl-aluminum was demonstrated by using different ketoesters. It is noteworthy that triallylaluminum is prepared from allyl bromide and aluminum metal, and not from a Grignard reagent, and that the procedure is operationally simple, leading to good to excellent product yields.
Indium-mediated one-pot three-component reaction of aromatic amines, enol ethers, and allylic bromides
Jang, Taeg-Su,Ku, Il Whea,Jang, Min Seok,Keum, Gyochang,Kang, Soon Bang,Chung, Bong Young,Kim, Youseung
, p. 195 - 198 (2007/10/03)
A new and efficient indium-mediated one-pot three-component reaction for the synthesis of N-aryl-substituted homoallylamines from aromatic amines, enol ethers, and allylic bromides in THF at room temperature is described.
Zirconium-Mediated Coupling Reactions of Amines and Enol or Allyl Ethers: Synthesis of Allyl- and Homoallylamines
Barluenga, Jose,Rodriguez, Felix,Alvarez-Rodrigo, Lucia,Zapico, Jose M.,Fananas, Francisco J.
, p. 109 - 116 (2007/10/03)
An easy and efficient zirconium-mediated synthesis of allylamines from simple amines and enol ethers is described. This strategy also allows the synthesis of amino alcohol derivatives containing a Z double bond in their structure when 2,3-dihydrofuran is used. Simple conventional modification of these amino alcohols leads to 2-substituted piperidine derivatives. By applying this approach, a formal total synthesis of the alkaloid coniine is easily achieved from a protected butylamine. Finally, the zirconium-mediated reaction of amines and allyl phenyl ether furnishes homoallylamines or amino ethers depending on the structure of the starting amine.
