124348-40-9Relevant articles and documents
Reaction of α,β-Unsaturated Imidates with Grignard Reagents Leading to 2-Alkyl 1,3-Diimines
Inoue, Seiichi,Suzuki, Osamu,Sato, Kikumasa
, p. 1773 - 1774 (1985)
Methyl N-phenylacrylimidate (1a) reacted with alkyl- and aryl-magnesium bromides in ether at O deg C to give 2-alkyl 1,3-diketones (3a) in a good yield after aqueous work-up; methyl N-phenylcrotonimidate (1b) and N-phenylcinnamimidate (1c) with alkylmagnesium bromides furnished analogous 1,3-diketones (3) as the major products after hydrolysis of the corresponding stable diimines (2).
Synthesis of Alkyl-Substituted 1,3-Diketones via the 1,4-Addition of the Grignard Reagents to α,β-Unsaturated Imidates
Inoue, Seiichi,Suzuki, Osamu,Sato, Kikumasa
, p. 1601 - 1605 (1989)
4-Propyl-3,5-nonanedione was selectively formed by the reaction of methyl N-phenylacrylimidate with ethylmagnesium bromide in 80percent yield.Similar diketones were obtained from methyl N-phenylcrotonimidate and N-phenylcinnamimidate with the Grignard reagents.The coupling of N-magnesio α-methoxy enamine and ketenimine, both of which are formed through the initial 1,4-addition of the Grignard reagent to α,β-unsaturated imidate, is the most plausible pathway for the formation of the diketones.
Direct conversion of cinnamate esters into β,β-disubstituted ketones mediated by cyano-magnesio cuprates
Genna, Douglas T.,Posner, Gary H.
, p. 5968 - 5971 (2016)
The clean synthesis of unsymmetrical ketones from carboxylic acid derivatives has been a challenge in the organic community dating back over 80 years. Herein we report the conversion of simple alkyl cinnamates to β,β-disubstituted ketones with cyano-magnesio cuprates in high yields with no observation of tertiary alcohol byproduct. The lack of tertiary alcohol is attributed to a putative enolate intermediate that serves as a ketone protecting group. A distinctive steric inhibition trend was observed related to both the size of the R group on the parent ester and the nucleophilic cuprate. Lastly, we demonstrate that this reaction can be coupled with known copper mediated allylic substitution reactions yielding β,γ-disubstituted ketone (8) from parent α-chloro-β,γ-ethylenic ester (7).
Chiral dinuclear phthalazine bridged bisoxazoline ligands: Synthesis and application in enantioselective Cu-catalyzed conjugate addition of ZnEt 2 to enones
Zhang, Liang,Yang, Guoqiang,Shen, Chaoren,Arghib, Sabah,Zhang, Wanbin
supporting information; experimental part, p. 2375 - 2378 (2011/05/09)
A new class of chiral dinuclear ligands with phthalazine bridged bisoxazoline scaffold was designed and prepared in convenient synthetic routes. 1H NMR analysis showed that this class of ligands could coordinate with two metal ions, either same
