Efficient synthesis of 1,3,5-trisubstituted (pyrrol-2-yl)acetic acid esters via dual nucleophilic reactions of sulfonamides or carbamate with 4-trimethyl-siloxy-(5E)-hexen-2-ynoates: Lewis acid catalyzed SN1 and intramolecular Michael addition
| Autor: | Toshiaki Aikawa, Teruhiko Ishikawa, Shinichiro Watanabe, Seiki Saito |
|---|---|
| Rok vydání: | 2006 |
| Předmět: |
Carbamate
medicine.medical_treatment Organic Chemistry General Medicine Conjugated system Biochemistry Medicinal chemistry Catalysis chemistry.chemical_compound Nucleophile chemistry Intramolecular force medicine Michael reaction Organic chemistry Lewis acids and bases Physical and Theoretical Chemistry Pyrrole |
| Zdroj: | Organic letters. 8(17) |
| ISSN: | 1523-7060 |
| Popis: | [reaction: see text] Carbamates or sulfonamides have proven to regioselectively attack 2-propynyl-allyl hybrid cations, generated by the action of TMSOTf on 4-(trimethylsioxy)hex-5-en-2-ynoates, to afford conjugated 6-aminohex-4-en-2-ynoates in which an intramolecular amino-Michael reaction took place, leading to pyrrole frameworks. In particular, the sulfonamides gave 1-sulfonylpyrroles in one pot. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|