410074-25-8Relevant academic research and scientific papers
Diastereofacial-selective synthesis of the trindane-based molecular scaffold cis,cis,cis-2,5,8-tribenzyltrindane-2,5,8-tricarboxylate and an arylamine analogue for the construction of C3v-symmetric architectures
Choi, Heung-Jin,Song, Jie,Chan, Young An,Nguyen, Quoc-Thiet,Kim, Hong-Seok
, p. 3290 - 3294 (2008/09/20)
Efficient syntheses of potentially valuable C3v-symmetric trindane-based triester scaffolds are reported. In the synthesis of 2,5,8-tribenzyltrindane-2,5,8-tricarboxylate by the benzylation of the corresponding triester by treatment with lithium diisopropylamide in tetrahydrofuran, the diastereoselectivity and yield of the cis,cis,cis- and cis,trans,trans-isomers depended primarily on the reaction temperature and the amount of hexamethylphosphoramide used as additive. High diastereofacial selectivity was achieved at -90°C in tetrahydrofuran, and the cis,cis,cis-isomer was obtained as the major product in 45% yield and in a diastereomeric ratio of 1.12. Under the same reaction conditions the 2,5,8-tris(4-bromobenzyl)trindane-2,5,8-tricarboxylate analogue was synthesized in 46% yield; it was efficiently converted into the 2,5,8-tris(4-aminobenzyl) trindane-2,5,8-tricarboxylate by palladium-catalyzed aromatic C-N bond formation by reaction with hexamethyldisilazide as nitrogen source in the presence of bis(dibenzylideneacetone)palladium with tri-tert-butylphosphine as catalyst in toluene. Georg Thieme Verlag Stuttgart.
Novel C3V-symmetric tripodal scaffold, triethyl cis,cis,cis-2,5,8- tribenzyltrindane-2,5,8-tricarboxylate, for the construction of artificial receptors.
Choi, Heung-Jin,Park, Yeon Sil,Yun, Seok Hun,Kim, Hong-Seok,Cho, Chan Sik,Ko, Kwangnak,Ahn, Kyo Han
, p. 795 - 798 (2007/10/03)
[reaction: see text] A novel C3V-symmetric scaffold, trindane 7, has been efficiently synthesized from 1,3,5-tris(bromomethyl)-2,4,6-tris(chloromethyl)benzene (1) in six steps with 47% overall yield. The control of all-syn stereochemistry in the tribenzyl
