16719-33-8Relevant academic research and scientific papers
Chirality memory of α-methylene-π-allyl iridium species
Cui, Yifan,Zhai, Yizhan,Xiao, Junzhe,Li, Can,Zheng, Wei-Feng,Huang, Chaofan,Wu, Guolin,Qin, Anni,Lin, Jie,Liu, Qi,Wang, Huanan,Wu, Penglin,Xu, Haibo,Zheng, Yangguangyan,Ma, Shengming
, p. 11831 - 11838 (2021)
Chirality is one of the most important types of steric information in nature. In addition to central chirality, axial chirality has been catching more and more attention from scientists. However, although much attention has recently been paid to the creation of axial chirality and the chirality transfer of allenes, no study has been disclosed as to the memory of such an axial chirality. The reason is very obvious: the chiral information is stored over three carbon atoms. Here, the first example of the memory of chirality (MOC) of allenes has been recorded, which was realizedviaan optically active alkylidene-π-allyl iridium intermediate, leading to a highly stereoselective electrophilic allenylation with amines. Specifically, we have established the transition metal-mediated highly stereoselective 2,3-allenylation of amines by using optically active 2,3-allenyl carbonates under the catalysis of a nonchiral iridium(iii) complex. This method is compatible with sterically bulky and small substituents on both amines and 2,3-allenyl carbonates and furnishes the desired optically active products with a high efficiency of chirality transfer. Further mechanistic experiments reveal that the isomerization of the optically active alkylidene-π-allyl iridium intermediate is very slow.
Synthesis and monoamine oxidase inhibitory activities of α-allenic amines in vivo and in vitro. Different activities of two enantiomeric allenes
Sahlberg,Ross,Fagervall,Ask,Claesson
, p. 1036 - 1042 (2007/10/02)
A series of 15 α-allenic amines, including primary, secondary, and tertiary ones, was synthesized, partly by organocopper chemistry. Their ability to inhibit mouse and rat brain mitochondrial monoamine oxidase (MAO) in vivo and in vitro, respectively, was
Allenes and Acetylenes. XXIV. Synthesis of α-Allenic Amines by Organocuprate Reactions of Acetylenic Aminoethers
Sahlberg, Christer,Claesson, Alf
, p. 179 - 186 (2007/10/02)
Tertiary α-allenic amines 1a - d are formed in good yields in reactions of acetylenic aminoethers with an organocuprate reagent, derived from butylmagnesium bromide and 5-20percent of CuI, in tetrahydrofuran (THF) or THF-diethyl ether 3:1.The overall redu
