Abstract
A series of new bidentate N,S-ligands—aziridines containing a para-substituted phenyl sulfide group—was synthesized and evaluated in the Pd-catalyzed Tsuji–Trost reaction and addition of diethylzinc and phenylethynylzinc to benzaldehyde. A high enantiomeric ratio for the addition reactions (up to 94.2:5.8) was obtained using the aziridine ligand bearing a p-nitro phenyl sulfide group. Collected results reveal a specific electronic effect that, by the presence of particular electron-donating or electron-withdrawing groups in the PhS- moiety, influences the σ-donor–metal binding and the enantioselectivity of the catalyzed reactions.
Highlights
Aziridines have established their position in modern organic synthesis thanks to a fortunate combination of properties—reactivity, stability and multidirectional transformability with high atom economy [1]
Thefirst firststep stepofof the research involved the synthesis tosylate1313 that was performed by a multistep procedure presented by Schneider et al
The first step of the research involved the synthesis of N-trityl aziridine tosylate 13 that was performed by a multistep procedure presented by Schneider et al [16] starting from L-serine methyl ester 9
Summary
Aziridines have established their position in modern organic synthesis thanks to a fortunate combination of properties—reactivity, stability and multidirectional transformability with high atom economy [1] These small heterocycles can be variously functionalized on the nitrogen or both carbon atoms and serve as stable intermediates, which, through a facile ring opening with various nucleophiles, can efficiently introduce a specific puzzle to a more complex molecule [2,3]. Their utility is even greater when chirality is considered.
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