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 solutions
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340
350
D.SCARPI; E.G.OCCHIATO; A.GUARNA
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2158/357250
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