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Synlett 1992; 1992(5): 451-452
DOI: 10.1055/s-1992-21378
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Synthesis of γ,δ-Unsaturated α-Methyl-α-amino Acids via Coupling of Allylsilanes with an α-Methylglycine Cation Equivalent

Eric C. Roos* , Henk Hiemstra, W. Nico Speckamp, Bernard Kaptein, John Kamphuis, Hans E. Schoemaker
  • *Department of Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, NL-1018 WS Amsterdam, The Netherlands
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Publication Date:
08 March 2002 (online)

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Intermolecular reactions of an α-methylglycine cation equivalent [methyl N-formyl-2-trimethylsiloxyalanine (6)] with allylsilanes, induced by trimethylsilyl trifluoromethanesulfonate, lead to protected γ,δ-unsaturated α-methyl-α-amino acids. A side reaction is the formation of a 2,3-dehydroalanine derivative 13, by proton loss from the cationic intermediate. The coupling products can be efficiently deprotected to the free α-amino acids.

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