10071-61-1Relevant academic research and scientific papers
Catalytic Desymmetrizing Dehydrogenation of 4-Substituted Cyclohexanones through Enamine Oxidation
Zhu, Lihui,Zhang, Long,Luo, Sanzhong
supporting information, p. 2253 - 2258 (2018/02/09)
A desymmetrizing dehydrogenation process catalyzed by a chiral primary amine is described herein. The reaction proceeds through the oxidation of a ketone enamine by IBX and enables the highly enantioselective desymmetrization of 4-substituted cyclohexanones with the generation of chiral 4-substituted cyclohexenones containing a remote γ-stereocenter.
ENANTIOSELECTIVE ROUTES TO 2,5-DISUBSTITUTED- AND 4-SUBSTITUTED-2-CYCLOHEXENONES
Asaoka, Morio,Aida, Toshiaki,Sonoda, Syuzo,Takei, Hisashi
, p. 7075 - 7078 (2007/10/02)
Starting with 5-trimethylsilyl-2-cyclohexenone, widely applicable enantioselective routes to the title compounds are established.
Regiocontrolled Synthesis of Mono-, Di, and Trisubstituted Cyclohexenones by Cycloaddition of Vinyl Sulfones to 1-Methoxy-3--1,3-butadienes. Conversion of Alkenes into Effective Dienophilic Reagents
Kinney, William A.,Crouse, Gary D.,Paquette, Leo A.
, p. 4986 - 5000 (2007/10/02)
Cycloaddition of phenyl vinyl sulfone to Danishefky's diene followed by direct ketalization provided 7, a synthon for the 4-(2-cyclohexenyl) anion.Thus, 7 readily undergoes regiospecific γ-alkylation.Ensuing reductive desulfonylation and hydrolysis provides 2-(and 3-)-cyclohexenones efficiently.Zingiberenol, a monocyclic sesquiterpene, was prepared by means of this methodology.Terminal alkenes and cyclic olefins enter into comparable regiocontrolled Diels-Alder addition if they are first subjected to selenosulfonation and oxidation to the vinyl sulfone.Removal of the phenylsulfonyl substituent after condensation provides the adducts which are formally derived from alkylation of the hypothetical C5 anion of 2-cyclohexenone.The scheme can be expanded to include γ-alkylation prior to desulfonylation.By this means, one is able to prepare 4,5-disubstituted 2-(and 3-)cyclohexenones where the nature of the pendant side chains can be widely varied.
A NEW SYNTHON FOR THE REGIOSPECIFIC γ-ALKYLATION OF 2-CYCLOHEXENONES. APPLICATION TO THE SYNTHESIS OF ZINGIBERENOL AND OXYGENATED BICYCLONONANES
Paquette, Leo A.,Kinney, William A.
, p. 131 - 134 (2007/10/02)
The regiospecific γ-alkylation of γ-sulfonylcyclohexenone ketals is described and applied to various synthetic objectives.
