27912-53-4Relevant academic research and scientific papers
Base-mediated cascade rearrangements of aryl-substituted diallyl ethers
Reid, Jolene P.,McAdam, Catherine A.,Johnston, Adam J. S.,Grayson, Matthew N.,Goodman, Jonathan M.,Cook, Matthew J.
, p. 1472 - 1498 (2015/02/19)
Two base-mediated cascade rearrangement reactions of diallyl ethers were developed leading to selective [2,3]-Wittig-oxy-Cope and isomerization-Claisen rearrangements. Both diaryl and arylsilyl-substituted 1,3-substituted propenyl substrates were examined, and each exhibits unique reactivity and different reaction pathways. Detailed mechanistic and computational analysis was conducted, which demonstrated that the role of the base and solvent was key to the reactivity and selectivity observed. Crossover experiments also suggest that these reactions proceed with a certain degree of dissociation, and the mechanistic pathway is highly complex with multiple competing routes.
NaH mediated isomerisation-allylation reaction of 1,3-substituted propenols
Johnston, Adam J. S.,McLaughlin, Mark G.,Reid, Jolene P.,Cook, Matthew J.
, p. 7662 - 7666 (2013/11/06)
A base mediated isomerisation-allylation protocol of 1,3-disubstituted propenols has been established. The use of diaryl and aryl-silyl substrates is reported alongside the use of substituted allyl bromides. Mechanistic experiments have also been conducted to elucidate the reaction pathway. The Royal Society of Chemistry 2013.
Stereoselective syntheses of allylic amines through reduction of 1-azadiene intermediates
Aguilar, Enrique,Joglar, Jesús,Merino, Isabel,Olano, Bernardo,Palacios, Francisco,Fustero, Santos
, p. 8179 - 8187 (2007/10/03)
The stereoselective synthesis of primary and secondary E-allylic amines by reduction of 1-azadiene intermediates is described. β-Enamino phosphonium salts are suitable starting materials to prepare secondary allylic amines. Two methods are reported for th
Mild and Regiospecific Reduction of Masked 1,3-Dicarbonyl Derivatives to Monocarbonyl Compounds and Primary and Secodary Amines
Barluenga, Jose,Aguilar, Enrique,Olano, Bernardo,Fustero, Santos
, p. 1741 - 1744 (2007/10/02)
The regiospecific reduction of masked 1,3-dicarbonyl compounds to the corresponding saturated monocarbonyl 3 or iminic 4 compounds via 3-amino-2-alkenimines 1 is described.The formation of 3 and 4 can be explained in terms of a double reduction process from 1.A simple method for the synthesis of primary and secondary amines 6 is also described.
