SmI2-Promoted novel tandem elimination and coupling reactions of aliphatic imides with carbonyl compounds: application to the synthesis of dl-isoretronecanol |
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Authors: | Masayuki Kabata |
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Affiliation: | Department of Molecular Science, Faculty of Engineering, Shizuoka University, Johoku 3-5-1, Hamamatsu 432-8561, Japan |
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Abstract: | Treatment of α-hetero-substituted cyclic imides with carbonyl compounds mediated by samarium(II) diiodide in the presence of HMPA was found to undergo novel tandem elimination and reductive coupling reactions to generate α-hydroxyalkylated imides in good to high yields. Stereochemistry of the coupling products was researched and the result that increasing the steric bulkiness of the N-substituents leads to an increase of threo-selectivity was observed. The mechanistic origins of this stereoselectivity are also briefly documented and the reaction was further applied to the convenient synthesis of a simple pyrrolizidine alkaloid, isoretronecanol. |
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Keywords: | SmI2 Reductive coupling Imide Pyrrolizidine alkaloid Isoretronecanol |
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