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Carbonyl compounds reactions with allenylsilanes

The reaction of allenylsilanes with electron deficient ir-systems constitutes a powerful and general method for the tegio- and stereo-selective preparation of substituted cyclopentenes. As first reported, (trimethylsilyl)allenes function as three-carbon nucleophiles in TiCU-promoted (trimethylsilyl)cyclopen-tene annelations (Scheme 31). The annelation process involves the polarization of an a,p-unsaturated carbonyl compound by TUTU to generate an alkoxyallylic cation. Regiospecific electnqrhilic substitution of this cation at C-3 of the allenylsilane produces a silicon-stablizied vinyl cation. A 1,2-shift of the tri-... [Pg.596]

The reaction of trimethylsilylallenes with aldehydes and ketones in the presence of titanium tetrachloride provides a regiocontrolled route to homopropargylic alcohols of a variety of substitution types. Thus, the addition of 1-alkyl-substituted trimethylsilylallenes to carbonyl compounds furnishes the desired alkynes directly, whereas reactions involving allenylsilanes initially produce mixtures of alkynes... [Pg.84]


See other pages where Carbonyl compounds reactions with allenylsilanes is mentioned: [Pg.447]    [Pg.596]    [Pg.596]    [Pg.596]    [Pg.314]   
See also in sourсe #XX -- [ Pg.596 ]

See also in sourсe #XX -- [ Pg.596 ]

See also in sourсe #XX -- [ Pg.596 ]




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Allenylsilane

Carbonyl compounds, reactions

Reaction with carbonyl compounds

Reactions with allenylsilanes

With Carbonyl Compounds

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