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Amines bearing diverse aryl substituents for potential utilities as energy and new materials have been synthesized from aziridine‐2‐carboxaldehyde and diverse aryl‐containing substrates. At first two aryl groups were to yield (aziridine‐2‐yl)‐1,1‐diaryl‐methane which was converted to 5‐diarylmethyl oxazolidin‐2‐one as a synthetic intermediate. They were further reacted with another aryl group in the presence of methanesulfonic acid to yield 2,3,3‐triarylpropylamine with the possible carbenium ion intermediate. In addition, this reaction with a second additional phenolic aryl group gave rise to the diversely substituted 3‐(4‐methoxyphenyl)‐(2,3‐dihydrobenzofuran‐2‐yl)methanamine derived from the intramolecular aziridine ring‐opening reaction by hydroxy group at phenol. [ABSTRACT FROM AUTHOR]

Alkaloids, asymmetric synthesis, aziridine, Mukaiyama aldol reaction, ZnCl2 mediated These -(aziridin-2-yl)- -hydroxy ketones were applied for the synthesis of various alkaloids including I epiallo i -isomuscarine, I epi i -enigmol, and I epi i -galantinic acid. Keywords: alkaloids; asymmetric synthesis; aziridine; Mukaiyama aldol reaction; ZnCl2 mediated EN alkaloids asymmetric synthesis aziridine Mukaiyama aldol reaction ZnCl2 mediated 1 1 1 01/20/22 20220101 NES 220101 B The straight forward b and highly diastereoselective synthesis of -(aziridin-2-yl)- -hydroxy ketones was achieved by the Mukaiyama aldol reaction of optically pure 1-( -methylbenzyl)-aziridine-2-carboxaldehyde and various enol-silanes in the presence of ZnCl SB 2 sb via a chelation-controlled transition state (98:2 dr, and >82% yields). [Extracted from the article]