131353-08-7Relevant academic research and scientific papers
Base-Induced Cyclization of α-Chloro- β,γ-Unsatured Ketones. Facile Synthesis of Tri- and Tetrasubstituted 2-Cyclopenten-1-ones
Mathew, Jacob
, p. 713 - 716 (2007/10/02)
Base-induced cyclization of fully substituted α-chloro β,γ-unsatured ketones results in substituted cyclopentenones.Potassium tert-butoxyde, lithium diisopropylamide, sodium hydroxide, and ammonium hydroxide can be used as the base for this process.In the case of ammonium hydroxide , it is proposed that initial formation of an enamine is followed by an intramolecular SN2'reaction of the enamine carbon.For all other bases, the reaction most likely proceeds through a ketone enolate.Application of this novel cyclization has been extended to the synthesis of several 2,3-substituted, 2,3,5-trisubstituted, and 2,3,5,5-tetrasubstituted 2-cyclopenten-1-ones.
A convergent Synthesis of Methylenomycin B and Analogues Via Selenium Assisted Cyclopenta-annelation
Mathew, Jacob
, p. 2039 - 2043 (2007/10/02)
Reaction of the lithium enolate of 4-chloro-4,5-dimethylhex-5-en-3-one 2 with benzeneselenenyl bromide at -78 deg C gives 2,3,5-trimethyl-5-phenylselenocyclopent-2-enone 3.Treatment of compound 3 with 15percent H2O2 in methylene dichloride at 0 deg C gave
