81770-99-2Relevant academic research and scientific papers
Synthesis of beta-substituted cyclopentenones via carbon alkylation of metalated gamma-methoxycyclopentenyl phenylsulfonyl anion
Kim, Seong Heon,Jin, Zhendong,Fuchs
, p. 4537 - 4538 (2007/10/02)
Metalation of γ-methoxyallyl sulfone 13 provides phenylsulfonyl anion 2a which undergoes alkylation followed by hydrolysis to afford β-substituted cyclopentenones.
NEW METHODS FOR β-CONJUGATE ADDITION AND β-HYDROXYALKYLATION OF ENONES
Kim, Sunggak,Lee, Phil Ho
, p. 5413 - 5416 (2007/10/02)
β-Conjugate addition and β-hydroxyalkylation of enones have been accomplished by the reaction of ylides, derivated from enones via phosphoniosilylation, with activated olefins and aldehydes in the presence of trimethylsilyl triflate in tetrahydrofuran at
Use of Protected β-Bromocyclopentenones and β-Bromocyclohexenones as β-Acylvinyl Anion Equivalents
Shih, Chuan,Swenton, John S.
, p. 2825 - 2832 (2007/10/02)
Ethylene glycol ketals of the 3-bromocyclohex-2-en-1-one as well as its 2-methyl, 2-n-propyl, and 5,5-dimethyl derivatives have been prepared, and their reactions with butyllithium were studied.The organolithium reagents derived from the above compounds react with a variety of electrophiles to afford after acid hydrolysis the corresponding 3-substituted cyclohexenones.Attempts to prepare the ethylene glycol ketal of 2-methyl-3-bromocyclopent-2-en-1-one gave a low yield of the bromoketal.However, dithioketals of 3-bromocyclopent-2-en-1-one and its 2-methyl derivativecould be prepared in good yield.The metalation chemistry of the dithioketals in both the five- and six-membered-ring series was examined.The functionalization chemistry of the resulting organolithium compounds afforded after dithioketal hydrolysis 3-functionalized cyclohex-2-en-1-ones and cyclopent-2-en-1-ones.Several limitations of the chemistry using allyl bromide and cyclohexenone as electrophiles are noted.
