Category: iodides-buliding-blocks. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Mesitylcopper(I), is researched, Molecular C9H11Cu, CAS is 75732-01-3, about Direct Catalytic Asymmetric Aldol Reaction of an α-Azido Amide. Author is Weidner, Karin; Sun, Zhongdong; Kumagai, Naoya; Shibasaki, Masakatsu.
α-Azido 7-azaindolinylamide I underwent diastereoselective and enantioselective aldol additions to ortho-substituted aryl aldehydes 2-RC6H4CHO (R = F3C, Br, I, O2N, PhCC, F) in the presence of mesitylcopper and either a nonracemic bis(diphenylphospholanyl)ethane or a nonracemic bis(diarylphosphino)binaphthalene ligand to yield either nonracemic syn- or anti-α-azido-β-hydroxy acyl 7-azaindolinylamides such as II (R = F3C, Br, I, O2N, PhCC, F; R1 = N3, H; R2 = H, N3) in 74-98% yields, 53:47->98:2 dr, and 89-99% ee. Aromatic aldehydes lacking ortho substituents underwent diastereoselective and enantioselective aldol addition reactions with I to yield syn-α-azido-β-hydroxy amides only. Alkynals underwent diastereoselective and enantioselective aldol addition reactions with I to yield anti-α-azido-β-hydroxy amides; aldol addition of I to hydrocinnamaldehyde gave product with no diastereo- or enantioselectivity. II (R = F3C; R1 = N3; R2 = H) was converted to the corresponding nonracemic α-azido-β-hydroxy carboxylic acid and Me carboxylate and to a nonracemic 3-aryl-2-aziridinecarboxylic acid; the 7-azaindoline byproduct could be recovered. The structures of II (R = F3C, PhCC; R1 = N3; R2 = H), an aziridine derived from II (R = F3C; R1 = N3; R2 = H), and the tert-Bu carbonate ester of a racemic anti-α-azido-β-hydroxy 7-azaindolinylamide derived from 3-(4-fluorophenyl)-2-propynal were determined by X-ray crystallog.
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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com