Search for Dipolarophile Structure Influence upon Stereochemistry of Cycloadducts in 1,3-Dipolar Cycloaddition of Azomethine Ylides Generated from N-(-)-Menthyloxycarbonylmethyl phenanthridinium
| Authors | |
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| Year of publication | 2001 |
| Type | Article in Proceedings |
| Conference | Book of Abstracts - 9th Meeting on Stereochemistry |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | 1;3-dipolar cycloaddition; chiral auxiliary; azomethine ylides; stereochemistry; structure |
| Description | Prepared (-)-menthyl - bromoacetate underwent a nucleophilic substitution reaction with the phenanthridine nitrogen atom under formation of N-(-)-menthyloxy-carbonylmethyl phenanthridinium.Generated azomethine ylides were searched in reactions with various olefines.Determination of relative configuration on atoms has been based on NMR measurements of interaction constants values. Non-symmetrical dipolarophiles are expected to form two regioisomers. Their formation has been determined by COSY and HMBC experiments based on H atoms interactions with carbonyl and nitrile carbon atom bound at C1 and C2 atoms, respectively. In all the cases only one regioisomer has been found. Chromatographically purified compounds were separated by HPLC on nonracemic sorbent based on cellulose. A detector UV (260 nm) and JASCO CD 995 (260 nm) for identification of enantiomers were used. |
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