75359-74-9Relevant articles and documents
A Silyl Enol Ether Variation of the Robinson Annulation
Huffman, John W.,Potnis, Shailesh M.,Satish, Amruthur V.
, p. 4266 - 4270 (1985)
The Lewis acid catalyzed reaction of regioselectively generated silyl enol ethers with vinyl ketones has been explored as an alternative to the Robinson annulation sequence.Alkylation of the trimethylsilyl enol ethers of cyclohexanone, 2-methylcyclohexanone, and 2,3-dimethylcyclohexanone with ethyl vinyl ketone, 3-penten-2-one, and methyl vinyl ketone ethylene ketal gave a series of 1,5-diketones.Cyclization of the diketones affords 2-octalones in fair to good overall yield.This procedure has been used to prepare in good yield 5,10-dimethyl-Δ1(9)-2-octalone, an important intermediate for sesquiterpene synthesis, with a cis/trans ratio of 3 to 1.Alkylation of the trimethylsilyl enol ether of isobutyraldehyde with 3-penten-2-one, methyl vinyl ketone, and its ethylene ketal followed by cyclization affords 4,4,5-trimethyl- and 4,4-dimethyl-2-cyclohexen-1-one.This method has been employed in the synthesis of 5-(hydroxymethyl)-2,4,4-trimethyl-2-cyclohexen-1-one, a potential synthon for ring A of the taxane diterpenes.
Organotin Triflate as Practical Catalyst for Michael Addition of Enol Silyl Ethers
Sato, Tsuneo,Wakahara, Yoshiyuki,Otera, Junzo,Nozaki, Hitosi
, p. 9773 - 9782 (2007/10/02)
Dibutyltin bis(triflate) is a mild Lewis acid which catalyzes clean Michael addition of enol silyl ethers.The new catalyst allows to employ various labile acceptors such as methyl vinyl ketone and 2-cyclopentenone which do not undergo smooth reaction with
LATENT ACETONYLATION OF α,β-ENONES WITH ALLYLTRIMETHYLSILANE OR 2-METHYL-2-PROPENYLTRIMETHYLSILANE: SYNTHESIS OF 1,5-DIKETONES AND ANNELATION TO FUSED CYCLOHEXENONES
Hosomi, Akira,Kobayashi, Hiroshi,Sakurai, Hideki
, p. 955 - 958 (2007/10/02)
Acetonylation of α,β-enones can be achieved by either with (2-methyl-2-propenyl)trimethylsilane or with allyltrimethylsilane followed by oxidative cleavage of the double bond or by the Wacker reaction, respectively.Annelation of the 1,5-diketones is also