Silyl enol ether

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Silyl enol ethers in organic chemistry are a class of organic compounds sharing a common functional group comprised of an enolate bonded through its oxygen terminus to an organosilicon group. The general structure is RR'C=C(R)OSi(R)₃.

Silyl enol ethers are important intermediates in organic synthesis.

[edit] Organic synthesis

• trimethylsilyl enol ethers can be prepared from ketones in presence of a strong base and trimethylsilyl chloride.
• Silyl enol ether can form by capturing any enolate formed in a nucleophilic conjugate addition. See ^[1] and ^[2] for an example.

[edit] Organic reactions

Silyl enol ethers react as nucleophiles in:

• Aldol reactions
• Michael reactions
• Alkylations
• Haloketone formation with halogens, for an example see ^[3]
• Acyloin formation by organic oxidation with mCPBA, for an example see ^[4]

[edit] References

1. ^ Organic Syntheses, Coll. Vol. 9, p.564 (1998); Vol. 73, p.123 (1996) Article
2. ^ Organic Syntheses, Coll. Vol. 8, p.277 (1993); Vol. 66, p. 43 (1988) Article.
3. ^ Organic Syntheses, Coll. Vol. 8, p.286 (1993); Vol. 69, p.129 (1990) Article
4. ^ Organic Syntheses, Coll. Vol. 7, p.282 (1990); Vol. 64, p.118 (1986) Article.