Tetrahedron

Synthesis of γ, δ,-unsaturated α-amino acids from allylsilanes and glycidyl cation equivalents

HH Mooiweer, H Hiemstra, WN Speckamp

Index: Mooiweer, Hendrik H.; Hiemstra, Henk; Speckamp, W. Nico Tetrahedron, 1989 , vol. 45, # 14 p. 4627 - 4636

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Citation Number: 44

Abstract

The 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- ...