Chiral Allylsilanes Derived from Naturally Occurring α-Amino Acids

Maurizio Franciotti; Alessandro Mordini; Maurizio Taddei

doi:10.1055/s-1992-21293

Synlett 1992; 1992(2): 137-138
DOI: 10.1055/s-1992-21293

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Chiral Allylsilanes Derived from Naturally Occurring α-Amino Acids

Maurizio Franciotti^* , Alessandro Mordini, Maurizio Taddei

^*Dipartimento di Chimica Organica "Ugo Schiff", Universitá di Firenze, Via G. Capponi 9,I-50121 Firenze, Italy

Abstract

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Natural occurring α-amino acids, N-butoxycarbonyl protected and converted into the corresponding aldehydes, were transformed into (Z)-alkenes 2-7 by Wittig olefination. Metalation with butyllithium-potassium tert-butoxide gave, after reaction with trimethylsilyl chloride, chiral allylsilanes [e.g., (Z)-(4S)-4-tert-butoxycarbonylamino-6-methyl-1-trimethylsilyl-2-heptene (10)]. The condensation of two of these with acetyl chloride-titanium(IV) chloride is also reported.

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