Synthesis of new C1-symmetric bis(oxazoline) ligands with a chelating sidearm for stereoselective Mukaiyama aldol condensations |
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| Authors: | Simonetta Orlandi,Gianmaria Dell&rsquo Anna |
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| Affiliation: | a Centro di Eccellenza CISI, Dipartimento di Chimica Organica e Industriale, via Golgi 19, I-20133 Milano, Italy
b Istituto di Chimica Organica, Facolta’ di Farmacia, Universita’ degli Studi di Milano, via Golgi 19, I-20133 Milano, Italy |
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| Abstract: | Novel C1-symmetric bis(oxazoline) ligands with a secondary binding sidearm were prepared in enantiomerically pure form in good yields, in only four steps starting from commercially available reagents. These new chiral ligands were tested in the enantioselective Mukaiyama aldol condensation between the trimethylsilyl keteneacetal of methyl isobutyrate and a non-chelating substrate such as benzaldehyde to afford the product in up to 55% ee. |
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| Keywords: | Chiral bis-oxazolines Copper complexes Enantioselective catalysis Mukaiyama aldol condensation Chelation |
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