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Relevant academic research and scientific papers

π-π Stacking versus steric effects in stereoselectivity control: Highly diastereoselective synthesis of syn-1,2-diarpropylamines

N-Arylarylideneamines react with sulfinylbenzyl carbanions derived from 2-(p-tolylsulfinyl)toluenes (S)-1 and (S)-2, affording epimeric mixtures at C1 of 1,2-diarylethyl- and 1,2-diarylpropylamine derivatives. The sulfinyl group completely controls the configuration at C2 in the reactions of (S)-2. The configuration at Cl depends on the electron density of the ring adjacent to the iminic carbon atom which is modulated by π-π stacking interactions with the ring joined to the carbanionic centre. The stereoselectivity was controlled by modifying the acceptor character of the arylideneamine ring with appropriate substituents, the formation of the highly selective (R) configuration at C1 being made possible by electron-donating groups. N-(2,4,6-Trimethoxyphenyl) arylideneamines have been shown to be suitable starting materials for the preparation of (R)-1,2-diarylethyl- and (1R,2S)-1,2-diarylpropylamines (syn epimers) in a highly stereoselective manner.

Highly stereoselective reactions of γ-sulfinyl carbanions with achiral imines

Lithium 2-p-tolylsulfinylbenzyl carbanions react with different N-substituted imines affording 1,2-diaryl ethyl (and propyl) amines with a high stereoselectivity control at both benzyllic (only dependent of the sulfur configuration) and iminic carbons. The anti:syn ratio, ranging between >96:98, dependent on the electronic density at nitrogen. Copyright Taylor & Francis Inc.

In vitro antifungal activity of new series of homoallylamines and related compounds with inhibitory properties of the synthesis of fungal cell wall polymers

The synthesis, in vitro antifungal evaluation and SAR studies of 101 compounds of the 4-aryl-, 4-alkyl-, 4-pyridyl or -quinolinyl-4-N-arylamino-1-butenes series and related compounds, are reported here. Active structures showed to inhibit (1,3)-β-D-glucan and mainly chitin synthases, enzymes that catalyze the synthesis of the major fungal cell wall polymers.

Oxidative carbon-carbon bond cleavage reaction of 1,2-diamines and 1,2-amino alcohols under an oxygen atmosphere

Under an atmosphere of oxygen 1,2-diamines underwent clean oxidative cleavage in the presence of BF3·OEt2 to give imines in good to excellent yields. 1,2-Amino alcohols were also cleaved under the same conditions to give imines and a