Chiral enantiopure bicyclic 1,4-aminoalcohols were synthesised by a new methodology that provided a common precursor which was easily N-functionalised with a wide variety of substituents. The final compounds were used as chiral ligands in a model study of the enantioselective addition of diethyl zinc to benzaldehyde, aimed at understanding the influence of the N-substituent on both rate and stereoselectivity of the reaction. This set of experiments also gave an interesting insight into the non-catalysed addition that occurred by employing commercially available Et2Zn solutions
N-Substituent effects on the diethylzinc addition to benzaldehyde catalysed by bicyclic 1,4-aminoalcohols / D.SCARPI; E.G.OCCHIATO; A.GUARNA. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - ELETTRONICO. - 20:(2009), pp. 340-350. [10.1016/j.tetasy.2009.01.021]
N-Substituent effects on the diethylzinc addition to benzaldehyde catalysed by bicyclic 1,4-aminoalcohols
SCARPI, DINA;OCCHIATO, ERNESTO GIOVANNI;GUARNA, ANTONIO
2009
Abstract
Chiral enantiopure bicyclic 1,4-aminoalcohols were synthesised by a new methodology that provided a common precursor which was easily N-functionalised with a wide variety of substituents. The final compounds were used as chiral ligands in a model study of the enantioselective addition of diethyl zinc to benzaldehyde, aimed at understanding the influence of the N-substituent on both rate and stereoselectivity of the reaction. This set of experiments also gave an interesting insight into the non-catalysed addition that occurred by employing commercially available Et2Zn solutionsFile | Dimensione | Formato | |
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