Synthesis of Clavulones (Claviridenones) via [3+2] Annulation Using Reaction of (β-(Phenylthio)acryloyl)silane with Lithium Enolate of Alkyl Methyl Ketone

Synlett ◽  
1997 ◽  
Vol 1997 (3) ◽  
pp. 255-256 ◽  
Author(s):  
Kei Takeda ◽  
Akemi Nakajima ◽  
Eiichi Yoshii
Keyword(s):  
Methyl Ketone ◽  
Lithium Enolate

Efficient Trapping of Ketone Enolates With Acrylate and β-Sulfonylacrylate Thioesters, β-Sulfonyl-, β-Sulfinyl- and β-Chloro-Vinyl Ketones; Facile Preparation of a Hydrindanone, cis-Dimethyloctalone, and Unsaturated 1,5-Dicarbonyl Compounds

1990 ◽  
Vol 43 (8) ◽  
pp. 1375 ◽  
Author(s):  
RJ Dancer ◽  
RK Haynes ◽  
WA Loughlin ◽  
SC Vonwiller
Keyword(s):  
Methyl Ketone ◽  
Conjugate Addition ◽  
Ring Closure ◽  
High Yield ◽  
Dicarbonyl Compounds ◽  
Lithium Enolate ◽  
Ketone Enolates ◽  
Facile Preparation

Tandem conjugate addition-ring closure involving reaction of the lithium enolate arising from conjugate addition of lithiated (E)-but-2- enyldiphenylphosphine oxide to 2-methyl-cyclopent-2-enone with two moles of t-butylthioacrylate generates a hydrindanol, and, in the presence of copper(I), a lactone derived from the hydrindanol. β-Sulfonylacrylate phenyl and t-butyl thioesters, β-chlorovinyl, β- sulfonyl- and β-sulfinyl-vinyl ketones react with the foregoing enolate, and with the enolate generated through conjugate addition of a methylcuprate to 2-methylcyclohexenone to give unsaturated 1,5-dicarbonyl compounds. The β-chlorovinyl ketones in particular react rapidly and in high yield. 2-Methylcyclohexenone has thereby been converted into a cis-dimethyl octalone; the conversion illustrates the effectiveness of β-chlorovinyl methyl ketone in the Robinson annelation. Reactions of the lithium enolate and titanium enol of 2,6- dimethylcyclohexanone with the β-substituted enones to give the corresponding unsaturated 1,5-dicarbonyl compounds and other products are also recorded.

The unexpected formation of a lithium-enolate from bis2-[(dimethylamino)methyl]phenyl copper lithium. X-ray structure of Li4[OC(CH2)C6H4CH2NMe2-2]4

1985 ◽  
Vol 292 (3) ◽  
pp. 319-324 ◽  
Author(s):  
Johann T.B.H. Jastrzebski ◽  
Gerard Van Koten ◽  
Martin J.N. Christophersen ◽  
Casper H. Stam
Keyword(s):  
Unexpected Formation ◽  
X Ray ◽  
Lithium Enolate ◽  
Methyl Phenyl

Ternary vapour-liquid equilibria system: Acetoneethyl methyl ketone-cyclohexane

2007 ◽  
Vol 7 (10) ◽  
pp. 535-543
Author(s):  
K. V. Kurmanadha Rao ◽  
V. V. G. Krishnamurty ◽  
C. Venkata Rao
Keyword(s):  
Methyl Ketone
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