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RESEARCH PRODUCT
Lewis Acid-Catalyzed [4 + 3] Cycloaddition of 2-(Trimethyl Silyloxy)acrolein with Furan. Insight on the Nature of the Mechanism from a DFT Analysis
José A. SáezManuel ArnóLuis R. Domingosubject
StereochemistryOrganic ChemistryAcroleinBiochemistryMedicinal chemistryCycloadditionCatalysischemistry.chemical_compoundResidue (chemistry)chemistryNucleophileFuranElectrophileLewis acids and basesPhysical and Theoretical Chemistrydescription
[reaction: see text]. The mechanism for the Lewis acid-catalyzed [4 + 3] cycloaddition of 2-(trimethylsilyloxy)acrolein 1 with furan 2 has been studied at the B3LYP/6-31G level. This reaction is a three-step process that is initialized by the nucleophilic attack of 2 to the beta-conjugated position of 1 to give a zwitterionic intermediate IN1. The key step on the formation of the seven-membered ring is the electrophilic attack of the furan residue to the electrophilically activated carbonyl carbon at this intermediate.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2003-10-24 | Organic Letters |