The Stereochemical Course of Nucleophilic Additions of 2-Trialkylsiloxyfurans to CyclicN-Acyliminium Ions
- 1 January 1992
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1992 (1/2) , 55-57
- https://doi.org/10.1055/s-1992-34157
Abstract
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.Keywords
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