Preparation and Structures of 2‐Substituted 5‐Benzyl‐3‐methylimidazolidin‐4‐one‐Derived Iminium Salts,Reactive Intermediates in Organocatalytic Transformations Involving α,β‐Unsaturated Aldehydes |
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| Authors: | Uro? Gro?elj Albert Beck W Bernd Schweizer Dieter Seebach |
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| Institution: | 1. Department of Organic Chemistry, Faculty of Chemistry and Chemical Technology, University of Ljubljana, A?ker?eva cesta 5, P.O. Box 537, SI‐1000 Ljubljana, (fax: +386?1?2419?220);2. Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zürich, H?nggerberg HCI, Vladimir‐Prelog‐Weg 3, CH‐8093 Zürich, (fax: +41?44?632?1144) |
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| Abstract: | Preparations of the title compounds, 5 – 7 (Scheme 1 and Table 1), of their ammonium salts, 9 – 11 (Scheme 2 and Table 2), and of the corresponding cinnamaldehyde‐derived iminium salts 12 – 14 (Scheme 3 and Table 3) are reported. The X‐ray crystal structures of 15 cinnamyliminium PF6 salts have been determined (Table 4). Selected 1H‐NMR data (Table 5) of the ammonium and iminium salts are discussed, and structures in solution are compared with those in the solid state. |
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| Keywords: | Organocatalysis Imidazolidinones Cinnamyl iminium salts Ammonium salts X‐Ray crystallography |
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