F-Butyl trimethylsilylacetate

Preparative Methods an advantage of f-butyl trimethylsilylacetate over its methyl and ethyl ester analogs is that it can be prepared by C-silylation of the lithium enolate of f-butyl acetate at —78 °C in THF (85-90% yield). Under the same conditions the enolates of methyl and ethyl acetate give primarily 0-silylated products. The reagent has also been prepared by a rapid boron trifluoride etherate catalyzed reaction of trimethylsilylketene with f-butyl alcohol. ... [Pg.147]

With cyclopentenone derivatives, 1,4-addition is observed for the ester enolates of methyl and f-butyl trimethylsilylacetate, although 1,2-addition occurs with acyclic conjugated enals. With a steroidal cyclopentenone substrate, both 1,2- and 1,4-addition were observed. Conjugate addition is observed for the methyl ester with chiral vinyl sulfoxides. High enantioselectivity can be attained (eq 7). ... [Pg.294]

Related Reagents. f-Butyl a-Lithiobis(trimethylsilyl)acetate f-Butyl Trimethylsilylacetate Ethyl Bromozincacetate Ethyl Lithioacetate Ethyl Trimethylsilylacetate Ketene Bis(trimethyl-silyl) Acetal Ketene f-Butyldimethylsilyl Methyl Acetal l-Methoxy-2-trimethylsilyl-l-(trimethylsilyloxy)ethylene Methyl (Methyldiphenylsilyl)acetate Methyl 2-Trimethylsilyl-acrylate Triethyl Phosphonoacetate Trimethylsilylacetic Acid. [Pg.294]

Related Reagents. f-Butyl Trimethylsilylacetate Dimethyl-2-(trimethylsilyl)acetamide Ethyl (Methyldiphenyl-silyl)acetate Ethyl Trimethylsilylacetate Trimethylsilylacetic Acid Trimethylsilylacetone. [Pg.297]

Related Reagents. f-Butyl a-Lithiobis(trimethylsilyl)acetate t-Butyl Trimethylsilylacetate Dilithioacetate Ethyl Lithio-(trimethylsilyl)acetate Ethyl Trimethylsilylacetate. [Pg.562]