Chiral Allylsilanes Derived from Naturally Occurring α-Amino Acids

Abstract

Natural occurring alpha-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.