N-Substituent effects on the diethylzinc addition to benzaldehyde catalysed by bicyclic 1,4-aminoalcohols

作者：Scarpi Dina^*; Occhiato Ernesto G; Guarna Antonio

来源：Tetrahedron: Asymmetry , 2009, 20(3): 340-350.

DOI：10.1016/j.tetasy.2009.01.021

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 the rate and stereoselectivity of the reaction. This set of experiments also provided interesting insight into the non-catalysed addition that Occurred by employing commercially available Et(2)Zn solutions.

• 出版日期2009-2-26