Publication

The regioselectivity of 1,3-disubstituted allylmetal species towards electrophiles. 1-(Trimethylsilyl)alk-2-enylpotassium compounds

Manfred Schlosser
1998
Journal Articles

Abstract

1-(Trimethylsilyl)alk-2-enylpotassium species are readily generated by deprotonation of (alk-2-enyl)trimethylsilanes with the superbasic mixt. of BuLi and KOCMe3. Like the parent compd., [1-(trimethylsilyl)allyl]potassium, they react with a variety of electrophiles preferentially, if not exclusively, at the silyl-distant terminus of the allyl moiety, thus producing branched ene silanes. The opposite regioselectivity previously obsd. with MeI hence appears to be an exception. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/a47e8ada-f742-4215-8bbb-4f4bbbe10e4f

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Manfred Schlosser
1998
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/a47e8ada-f742-4215-8bbb-4f4bbbe10e4f

About this result

Related concepts (2)

Silyl enol ether

Silyl enol ethers in organic chemistry are a class of organic compounds that share a common functional group composed of an enolate bonded through its oxygen end to an organosilicon group. They are important intermediates in organic synthesis. Silyl enol ethers are generally prepared by reacting an enolizable carbonyl compound with a silyl electrophile and a base, or just reacting an enolate with a silyl electrophile. Since silyl electrophiles are hard and silicon-oxygen bonds are very strong, the oxygen (of the carbonyl compound or enolate) acts as the nucleophile to form a Si-O single bond.

Aldol reaction

The aldol reaction (aldol addition) is a reaction that combines two carbonyl compounds (aldehydes or ketones) to form a new β-hydroxy carbonyl compound. These products are known as aldols, from the aldehyde + alcohol, a structural motif seen in many of the products. The use of aldehyde in the name comes from its discovery history, where aldehydes were first used in the reaction and not ketones. Aldol structural units are found in many important molecules, whether naturally occurring or synthetic.