Abstract
Functionalizable salen derivative, 6,6'-(1E,1'E)-((1R,2R)-1,2-diphenylethane-1,2-diyl)bis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)bis(2-tert-butyl-4-((trimethylsilyl) ethyn-yl)phenol) (3), was synthesized by condensation between (1R,2R)-1,2-diphenylethane-1,2-diamine (2) and 3-tert-butyl-2-hydroxy-5-((trimethylsilyl)ethynyl) benzaldehyde (1) under refluxing conditions. The title compound was characterized by 1H-NMR, 13C-NMR, FT-IR, high-resolution mass spectrometry, optical rotation and melting point determination.
Highlights
N,N'-Bis(salicylidene)ethylidenediamines, more commonly referred to as salen molecules, constitute one of the most popular and useful ligands for catalysts used in asymmetric synthesis [1]
The title compound 3 was obtained in 87% yield via the nucleophilic addition of (1R,2R)-1,2diphenylethane-1,2-diamine (2) to 5-(trimethylsilyl)ethynyl-3-tert-butyl-2-hydroxybenzaldehyde (1), which was previously synthesized following the method reported by Seebach and co-workers [10]
To Jürgen Bachl (Universität Regensburg) and Javier Sayago (Universidad de Zaragoza) for their valuable assistance
Summary
N,N'-Bis(salicylidene)ethylidenediamines, more commonly referred to as salen molecules, constitute one of the most popular and useful ligands for catalysts used in asymmetric synthesis [1].Since the first metallated salen ligand reported independently by Jacobsen [2] and Katsuki [3], which continues being the most efficient catalyst for a wide variety of organic reactions [ ], a plethora of different chiral salen ligands has been comprehensively studied. Institut für Organische Chemie, Universität Regensburg, Universitätsstr. H-NMR, 13C-NMR, FT-IR, high-resolution mass spectrometry, optical rotation and melting point determination. N,N'-Bis(salicylidene)ethylidenediamines, more commonly referred to as salen molecules, constitute one of the most popular and useful ligands for catalysts used in asymmetric synthesis [1].
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