Effect of intramolecular interactions on circular dichroism of ortho‐substituted 1‐phenethylamines

Abstract

The synthesis of ortho-substituted (S)-1-phenethylamines via ortho-lithiation of its N,N-dimethyl derivative followed by reactions with different reagents is described. Circular dichroism spectra of synthesized compounds were measured. It is shown that the observed short-wave Cotton effects greatly depend on the existence of cyclic structure due to possible interactions such as hydrogen bond or electrostatic interaction.

Chiral halogenated Schiff base compounds: green synthesis, anticancer activity and DNA-binding study

“…The CD spectra of the two enantiomers of a chiral molecule are of equal magnitude and opposite sign: i.e., mirrorimage enantiomers give mirror-image CD spectra [30]. Although it is expected that the CD spectrum of the two enantiomers must be equal magnitude and opposite sign, sometimes factors such as solvent variation, inter-and intramolecular interaction or the presence of a particular substituent in the compounds does not allow the expected spectrum to occur and causes some changes in the CD spectrum [31,32]. CD spectra of the synthesized chiral compounds are shown in Fig.…”

New chiral amino alcohol ligands derived from 1-phenylethylamine for efficient Ru-catalyzed asymmetric transfer hydrogenation

“…8 The treatment of (S)-1-phenylethylamine with n-BuLi at À35°C, followed by a slow addition of neat Me 3 SiCl, generated the monosilylated product, N-(trimethylsilyl)-1-phenylethylamine in situ. 9 The latter was dilithiated by further addition of 3 equiv of n-BuLi at À35°C and then quenched with a variety of carbonyl compounds including formaldehyde, acetone, cyclohexanone, and benzophenone.…”

“…8,47.1,82.4,126.4,126.7,126.8,126.9,127.3,127.7,127.8,128.6,130.7,142.3,146.9,147.9,149.1;HRMS (m/z) …”