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Issue 12, 1999
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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

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.

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Article type: Paper
DOI: 10.1039/A902789K
Chem. Commun., 1999, 1075-1076

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    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

    Y. Masuyama, J. Tosa and Y. Kurusu, Chem. Commun., 1999, 1075
    DOI: 10.1039/A902789K

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