The stereochemical course of nucleophilic additions of 2-trialkylsiloxyfurans to cyclic N-acyliminium ions

DOI: 10.1055/s-1992-34157

Source and publish data:

Synthesis p. 55 - 57 (1992)

Update date:2022-08-05

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Authors:

Martin Martin

Corbett Corbett

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Article abstract of DOI:10.1055/s-1992-34157

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 treo-9/erythro-9, respectively, in which the threo diastereoisomers dominated by ratios of 8.5-6:1.

Full text of DOI:10.1055/s-1992-34157

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