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Synthesis 1992; 1992(1/2): 55-57
DOI: 10.1055/s-1992-34157
short paper
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The Stereochemical Course of Nucleophilic Additions of 2-Trialkylsiloxyfurans to Cyclic N-Acyliminium Ions

Stephen F. Martin* , Jeffrey W. Corbett
  • *Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA
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Publication Date:
18 September 2002 (online)

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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.