Imine allylation by allylic trimethylsilanes via in situ formation of N-tosyliminium species from carbonyl compounds and toluene-p-sulfonamide with SnCl2 and N-chlorosuccinimide: regioselection and diastereoselection
- 1 January 1999
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 12,p. 1075-1076
- https://doi.org/10.1039/a902789k
Abstract
N-Tosyliminium species, prepared in situ from carbonyl compounds and TsNH2 with SnCl2 and N-chlorosuccinimide, undergo nucleophilic addition of allylic silanes (imine allylation) to produce the corresponding homoallylic amines; the imine allylation by but-2-enyltrimethylsilane with aldehydes and TsNH2 leads to regio- and diastereo-selection to produce anti 1-substituted 2-methylbut-3-enylamines.Keywords
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