Silicon Polonovski Reaction. Formation and Synthetic Application of α-Siloxy Amines
A new and versatile synthetic intermediate, α-siloxy amine was prepared in situ by the base-promoted rearrangement of a siloxyammonium salt obtained by treatment of a tertiary amine N-oxide with trialkylsilyl trifluoromethanesulfonate.The best combination of the base and silylating reagent was found to be methyllithium and t-butyldimethylsilyl trifluoromethanesulfonate.The reactions of α-siloxy amines with acyl halides and haloformates gave the corresponding amides and carbamates in moderate to good yields, respectively.Treatment of α-siloxy amines with acetic acid resulted in a direct dealkylation to free secondary amines.Fluoride induced alkylation of α-siloxy amines using alkyl halides as electrophiles leading to tertiary amines was also examined and demonstrated to be a new transalkylation method of amines.
Tokitoh, Norihiro,Okazaki, Renji
p. 3291 - 3298
(2007/10/02)
Amino-acids and peptides. XXIV. The use of esters of 1-hydroxypiperidine and of other NN-dialkylhydroxylamines in peptide synthesis and as selective acylating agents.
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Handford,Jones,Young,Johnson
p. 6814 - 6827
(2007/10/04)
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