1252575-90-8Relevant academic research and scientific papers
Highly Selective Nucleophilic 4-Aryl-2,3-allenylation of Malonates?
Song, Shihua,Ma, Shengming
, p. 1233 - 1238 (2020)
Allenes are a class of very important compounds and the development of straightforward, efficient, and highly enantioselective synthetic strategies for allenes have attracted extensive interests. Along this line, it is well known that aryl-substituted allenes may be readily racemized, thus, difficult to prepare in high ee. Herein, an efficient palladium-catalyzed nucleophilic allenylation of malonates with racemic 4-aryl-2,3-butadienyl carbonates has been developed. The selectivity issue of mono- vs. bis-allenylation with 2-non-substituted malonates has been addressed. By utilizing (R)-(–)-DTBM-SEGPHOS (5,5'-bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole) as a chiral ligand, various aryl-substituted allenes and bisallenes have been prepared with good to excellent yields with high chemoselectivity and enantioselectivity under mild reaction conditions. Au-catalyzed cycloisomerization and APK (allenic Pauson–Khand) reactions affording optically active mono- and bicyclic products have been demonstrated.
Gold-catalyzed N, O-functionalizations of 6-allenyl-1-ynes with n-hydroxyanilines to construct benzo[b]-azepin-4-one cores
Raj, Antony Sekar Kulandai,Kale, Balaji S.,Mokar, Bhanudas Dattatray,Liu, Rai-Shung
supporting information, p. 5340 - 5343 (2017/11/07)
Gold-catalyzed reactions of 6-allen-1-ynes with N-hydroxyanilines afford thermally stable benzoazepin-4-ones in anti-selectivity; these anti-configured products are easily isomerized to their syn-isomers on a silica column. The mechanism of reactions likely involve initial nitrone/allene cycloadditions, followed by skeletal rearrangement of resulting intermediates.
A Versatile Room-Temperature Route to Di- and Trisubstituted Allenes Using Flow-Generated Diazo Compounds
Poh, Jian-Siang,Tran, Duc N.,Battilocchio, Claudio,Hawkins, Joel M.,Ley, Steven V.
, p. 7920 - 7923 (2015/06/30)
A copper-catalyzed coupling reaction between flow-generated unstabilized diazo compounds and terminal alkynes provides di- and trisubstituted allenes. This extremely mild and rapid transformation is highly tolerant of several functional groups. Well tolerated: A mild copper-catalyzed coupling reaction between unstabilized diazo compounds (generated in flow) and terminal alkynes is reported. The method provides di- and trisubstituted allenes with high functional-group tolerance.
