(L)-(Trimethylsilyl)alanine synthesis exploiting hydroxypinanone-induced diastereoselective alkylation |
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Authors: | A René N Vanthuyne J Martinez F Cavelier |
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Institution: | 1. IBMM, UMR-CNRS-5247, Universités Montpellier I and II, Place Eugène Bataillon, 34095, Montpellier, France 2. Chirosciences, ISm2,UMR-7313, Aix-Marseille Université, Avenue Escadrille Normandie Niémen, 13397, Marseille, France
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Abstract: | A new and efficient synthesis of (L)-(trimethylsilyl)alanine (TMSAla) with suitable protection for use in Solid Phase Peptide Synthesis (SPPS) has been accomplished starting from glycine tert-butyl ester and using hydroxypinanone as chiral inductor. The silylated side chain was introduced by alkylation of the Schiff base intermediate with iodomethyl(trimethylsilane) at ?78 °C. Among the different synthetic routes that were tested including several chiral inductors and different Schiff bases, this strategy was selected and afforded (L)-TMSAla in good chemical overall yield with 98 % ee. |
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