Synthesis of γ,δ,-unsaturated α-amino acids from allylsilanes and glycidyl cation equivalents
1989; Elsevier BV; Volume: 45; Issue: 14 Linguagem: Inglês
10.1016/s0040-4020(01)89098-0
ISSN1464-5416
AutoresH. H. MOOIWEER, Henk Hiemstra, W. N. SPECKAMP,
Tópico(s)Fluorine in Organic Chemistry
ResumoThe synthesis of a series of γ,δ-unsaturated N-protected α-amino acid methyl esters from the coupling of different allylsilanes and glycidyl cation equivalents 6 and 7 is described. Reactions with methoxyglycine derivative 6 are induced with BF3·OEt2; in the case of chloroglycine derivative 7 SnCl4 is used as Lewis acid. Reactions are fully regioselective, but show low stereoselectivity. The conversion of the reaction products into unprotected α-amino acids is described for two cases.
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