Assignments got your hair on fire?

Douse the flames with our full-range writing service!

Experienced academic writing professionals are at your fingertips. Use this handy tool to get a price estimate for your project.

Silyl enol ether synthesis by silylation - Organic chemistry

The use of a functionalized dipolarophile, such as a silyl enol ether (e.g., 1) or a vinyl silane, would provide a silyl-protected hydroxyl group that could be revealed and manipulated as needed or an alkyl silane that could be oxidized to the corresponding hydroxyl group.

The primary goal is to explore the scope and utility of silyl enol ethers as two-carbon dipolarophiles in intramolecular oxidopyrylium ylide [5C+2C] dipolar cycloadditions (Figure 1).

Protection of the alcohol as a THP ether followed by silylcupration afforded the ()-vinyl silane 8.

Synthesis of ethers - Organic chemistry

T1 - Acylation of ketone silyl enol ethers with acid chlorides. Synthesis of 1,3-diketones

Silyl ethers will be cleaved by nucleophiles (especially oxygen and fluoride) to form Si-O/F bonds – F is therefore particularly effective because it is small and generally unreactive. They may also be cleaved under a range of acidic and basic conditions. It should be noted that the large range of available silyl ethers display a large range of sensitivity to acid and base (too large to go into here!) which means that careful choice of ether and conditions can ensure only the targeted protecting groups are cleaved when you wish.

For the very bulky silyl reagents, a catalytic amount of (labelled below) is needed to speed up their reaction with the hydroxyl. This increase in rate is due to the formation of a reactive ;

Synthesis of novel silyl enol ethers from..

There are many other tri-alkyl-silyl-chloride besides TMSCl which are far more bulky. Their bulkiness increases their selectivity in formation of silyl ethers and also makes them more difficult to remove. Some commonly encountered silyl reagents;

Using the same THP ether 7, as described above, the terminal alkyne was silylated to give 11 (Scheme 2).

AB - Optically active α-hydroxy ketones 3 have been prepared in moderate to high enantioselectivities by the asymmetric oxidation of the silyl enol ethers 2 with in situ generated dioxirane from the fructose-derived ketone 1. Best results (ee values up to 82%) for this novel non-transition metal mediated asymmetric α-hydroxylation may be obtained, when an excess of the fructose-derived ketone 1 is employed at pH ca. 8 and short reaction times. Valuable mechanistic information on the spiro versus planar transition states for the oxygen-transfer process has been aquired through the absolute configuration of the resulting α-hydroxy ketone 3 products.

Versatile Services that Make Studying Easy
We write effective, thought-provoking essays from scratch
We create erudite academic research papers
We champion seasoned experts for dissertations
We make it our business to construct successful business papers
What if the quality isn’t so great?
Our writers are sourced from experts, and complete an obstacle course of testing to join our brigade. Ours is a top service in the English-speaking world.
How do I know the professor won’t find out?
Everything is confidential. So you know your student paper is wholly yours, we use CopyScape and WriteCheck to guarantee originality (never TurnItIn, which professors patrol).
What if it doesn’t meet my expectations?
Unchanged instructions afford you 10 days to request edits after our agreed due date. With 94% satisfaction, we work until your hair is comfortably cool.
Clients enjoy the breezy experience of working with us
Click to learn our proven method

Silyl ethers are a group of chemical compounds which ..


A Practical Method for the Preparation of Trimethylsilyl Enol ..

N2 - Optically active α-hydroxy ketones 3 have been prepared in moderate to high enantioselectivities by the asymmetric oxidation of the silyl enol ethers 2 with in situ generated dioxirane from the fructose-derived ketone 1. Best results (ee values up to 82%) for this novel non-transition metal mediated asymmetric α-hydroxylation may be obtained, when an excess of the fructose-derived ketone 1 is employed at pH ca. 8 and short reaction times. Valuable mechanistic information on the spiro versus planar transition states for the oxygen-transfer process has been aquired through the absolute configuration of the resulting α-hydroxy ketone 3 products.

for the Preparation of Trimethylsilyl Enol Ethers ..

(Chemical Equation Presented) Unsymmetrical silyl bis-enol ethers have been developed as effective substrates for synthesizing quaternary centers from tetralone derivatives through oxidative carbon-carbon bond formation. The derived products are shown to be highly versatile intermediates that may be used to generate diverse structures such as cyclopentenones, 2H-pyrroles, and spirocyclic pyrrolidines.

Synthesis of Silyl Enol Ethers.

N2 - Trimethylsilyl enol ethers of ketones are acylated by a variety of acid chlorides in the presence of zinc chloride or antimony trichloride. The major product of this reaction is the 1,3-diketone resulting from C-acylation. Some O-acylation is observed in most cases. Yields of 1,3-diketones varied but were usually good to excellent.

Synthesis of Silyl Enol Ethers by Mg/TMSCl | Tvv2012's …

Trimethylsilyl enol ethers of ketones are acylated by a variety of acid chlorides in the presence of zinc chloride or antimony trichloride. The major product of this reaction is the 1,3-diketone resulting from C-acylation. Some O-acylation is observed in most cases. Yields of 1,3-diketones varied but were usually good to excellent.

This page looks at the formation and activities of Silyl Enol Ethers.

AB - Trimethylsilyl enol ethers of ketones are acylated by a variety of acid chlorides in the presence of zinc chloride or antimony trichloride. The major product of this reaction is the 1,3-diketone resulting from C-acylation. Some O-acylation is observed in most cases. Yields of 1,3-diketones varied but were usually good to excellent.

Electrophilic Reactions of Silyl Enol Ethers | SpringerLink

N2 - (Chemical Equation Presented) Unsymmetrical silyl bis-enol ethers have been developed as effective substrates for synthesizing quaternary centers from tetralone derivatives through oxidative carbon-carbon bond formation. The derived products are shown to be highly versatile intermediates that may be used to generate diverse structures such as cyclopentenones, 2H-pyrroles, and spirocyclic pyrrolidines.

See also Silyl enol ether References Clayden ..

AB - (Chemical Equation Presented) Unsymmetrical silyl bis-enol ethers have been developed as effective substrates for synthesizing quaternary centers from tetralone derivatives through oxidative carbon-carbon bond formation. The derived products are shown to be highly versatile intermediates that may be used to generate diverse structures such as cyclopentenones, 2H-pyrroles, and spirocyclic pyrrolidines.

89%
of clients claim significantly improved grades thanks to our work.
98%
of students agree they have more time for other things thanks to us.
Clients Speak
“I didn’t expect I’d be thanking you for actually improving my own writing, but I am. You’re like a second professor!”