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Efficient Pyrrole Synthesis Using Double Nucleophilic Addition to α,β-Unsaturated Imines with Plural Nucleophiles

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journal contribution
posted on 03.08.2006, 00:00 by Makoto Shimizu, Atsushi Takahashi, Shiho Kawai
2,3,5-Trisubstituted pyrroles were prepared in a regioselective manner using the double nucleophilic addition of α,α-dialkoxy ketene silyl acetals and ketene sily thioacetals or trimethylsilyl cyanide to α,β-unsaturated imines followed by acid-promoted cyclization and oxidation with DDQ. Using this methodology an imidazole glycerol phosphate dehydratase inhibitor (IGPDI) possessing a monopyrrole aldehyde moiety was synthesized.