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The Stereochemical Course of Nucleophilic Additions of 2-Trialkylsiloxyfurans to Cyclic<i>N</i>-Acyliminium Ions
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1992
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HeterocyclicBiochemistryCyclic N-acyliminium IonNatural SciencesOrganic ChemistryStereochemical CourseOrganometallic CatalysisThreo DiastereoisomersChemistryStereoselective SynthesisDerivative (Chemistry)Synthetic ChemistryNucleophilic Additions
The additions of 2-(trimethylsiloxy)furan (5) and 2-(tert-butyldimethylsiloxy) -3-methylfuran (6) to the cyclic N-acyliminium ion generated upon treatment of 1-benzyloxycarbonyl-2-ethoxypyrrolidine (7) with diethyl ether-boron trifluoride complex afforded mixtures of adducts threo-8/erythro-8 and threo-9/erythro-9, respectively, in which the threo diastereoisomers dominated by ratios of 8.5-6:1.