Synthesis of a Novel C2‐Symmetric Bis‐oxazoline (=Bis[4,5‐dihydrooxazole]) and Its Application as Chiral Ligand in Asymmetric Transition Metal Catalysis |
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| Authors: | Yaşar Gök Johan Van der Eycken |
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| Institution: | 1. Laboratory for Organic and Bioorganic Synthesis, Department of Organic Chemistry, Ghent University, Krijgslaan 281 (S.4), B‐9000 Ghent;2. Department of Chemistry, Faculty of Arts and Sciences, Osmaniye Korkut Ata University, Karacaoglan Yerleskesi, 80000 Osmaniye, Turkey, (phone: +90‐328‐8271000/2541;3. fax: +90‐328‐8250097) |
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| Abstract: | The new C2‐symmetric bis‐oxazoline (=bis4,5‐dihydrooxazole]) 2 with a chiral trans‐(2R,3R)‐2,3‐bis(3,5‐diphenylphenyl)cyclopropylidene (=trans‐(2R,3R)‐2,3‐bis(1,1′: 3′,1″‐terphenyl]‐5′‐yl)cyclopropylidene) backbone was efficiently synthesized (Scheme). All synthetic steps were easy to perform and led to the desired product in good overall yields. Compound 2 was tested and compared as ligand in several enantioselective catalytic reactions such as palladium(0)‐catalyzed enantioselective allylic alkylations and copper(I)‐catalyzed enantioselective cyclopropanations and aziridinations. |
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| Keywords: | Bis‐oxazolines Enantioselective synthesis Catalysis Copper complexes Palladium complexes |
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