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.
Franciotti, M., Mordini, A., Taddei, M. (1992). Chiral Allylsilanes Derived From Naturally-occurring Alpha-amino-acids. SYNLETT, 1992(2), 137-138 [10.1055/s-1992-21293].
Chiral Allylsilanes Derived From Naturally-occurring Alpha-amino-acids
Taddei, Maurizio
1992-01-01
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.
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https://hdl.handle.net/11365/30960
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