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Silyl enol ether



  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.

Silyl enol ethers are important intermediates in organic synthesis.

Additional recommended knowledge

Contents

Organic synthesis

Organic reactions

Silyl enol ethers react as nucleophiles in:

Saegusa oxidation

In the Saegusa oxidation certain silyl enol ethers are oxidized to enones with palladium(II) acetate. In the original publication [5] the amount of palladium is less than stochiometric and 1,4-benzoquinone is used as sacrificial catalyst. The intermediate is an oxo-allylpalladium complex.

In one application a dienenone is synthesized in two steps from a cyclohexanone [6] [7]:

Ketene silyl acetals

Ketene silyl acetals are related compounds formally derived from ketenes and acetals with general structure R-C=C(OSiR3)(OR').

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.
  5. ^ Synthesis of alpha, beta-unsaturated carbonyl compounds by palladium(II)-catalyzed dehydrosilylation of silyl enol ethers Yoshihiko Ito, Toshikazu Hirao, and Takeo Saegusa J. Org. Chem.; 1978; 43(5) pp 1011 - 1013; doi:10.1021/jo00399a052
  6. ^ Formation of Benzo-Fused Carbocycles by Formal Radical Cyclization onto an Aromatic Ring Derrick L. J. Clive and Rajesh Sunasee Org. Lett.; 2007; 9(14) pp 2677 - 2680; (Letter) doi:10.1021/ol070849l
  7. ^ reagents in step 1 are trimethylsilyl triflate and 2,6-lutidine
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Silyl_enol_ether". A list of authors is available in Wikipedia.
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