119414-47-0Relevant articles and documents
Cis and trans selective 1,4-addition of a lithium dithioester enolate to 4-O-TBS-2-cyclohexenone
Spivey, Alan C.,Martin, Laetitia J.,Grainger, Damian M.,Ortner, Joerg,White, Andrew J. P.
, p. 3891 - 3894 (2006)
The 1,4-addition of the lithium enolate of methyldithioacetate (LMDTA) to (±)-4-O-TBS-2-cyclohexenone (3) can be varied from being highly 3,4-trans selective to being highly 3,4-cis selective simply by varying the reaction temperature. This stereodivergen
Electrochemically driven desaturation of carbonyl compounds
Gnaim, Samer,Takahira, Yusuke,Wilke, Henrik R.,Yao, Zhen,Li, Jinjun,Delbrayelle, Dominique,Echeverria, Pierre-Georges,Vantourout, Julien C.,Baran, Phil S.
, p. 367 - 372 (2021/03/31)
Electrochemical techniques have long been heralded for their innate sustainability as efficient methods to achieve redox reactions. Carbonyl desaturation, as a fundamental organic oxidation, is an oft-employed transformation to unlock adjacent reactivity through the formal removal of two hydrogen atoms. To date, the most reliable methods to achieve this seemingly trivial reaction rely on transition metals (Pd or Cu) or stoichiometric reagents based on I, Br, Se or S. Here we report an operationally simple pathway to access such structures from enol silanes and phosphates using electrons as the primary reagent. This electrochemically driven desaturation exhibits a broad scope across an array of carbonyl derivatives, is easily scalable (1–100 g) and can be predictably implemented into synthetic pathways using experimentally or computationally derived NMR shifts. Systematic comparisons to state-of-the-art techniques reveal that this method can uniquely desaturate a wide array of carbonyl groups. Mechanistic interrogation suggests a radical-based reaction pathway. [Figure not available: see fulltext.]
Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones
Diao, Tianning,Stahl, Shannon S.
supporting information; experimental part, p. 14566 - 14569 (2011/10/17)
α,β-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. Here, we report the discovery and application of Pd(DMSO)2(TFA)2 as a catalyst for direct dehydrogenation of cyclohexanones and other cyclic ketones to the corresponding enones, using O2 as the oxidant. The substrate scope includes heterocyclic ketones and several natural-product precursors.
The synthesis of 2-oxyalkyl-cyclohex-2-enones, related to the bioactive natural products COTC and antheminone A, which possess anti-tumour properties
Arthurs, Claire L.,Morris, Gareth A.,Piacenti, Michela,Pritchard, Robin G.,Stratford, Ian J.,Tatic, Tanja,Whitehead, Roger C.,Williams, Katharine F.,Wind, Natasha S.
experimental part, p. 9049 - 9060 (2011/01/04)
The syntheses of five novel 2-oxyalkyl-cyclohex-2-enones, structurally related to the natural products COTC and antheminone A, are described. The target structures were selected in order to probe the influence of several key structural parameters on in vi
An efficient protocol for the enantioselective preparation of a key polyfunctionalized cyclohexane. New access to (R)- and (S)-4-hydroxy-2- cyclohexenone and (R)- and (S)-trans-cyclohex-2-ene-1,4-diol
Bayon, Pau,Marjanet, Georgina,Toribio, Gladis,Alibes, Ramon,De March, Pere,Figueredo, Marta,Font, Josep
, p. 3486 - 3491 (2008/09/21)
(Chemical Equation Presented) Starting from very accessible raw materials such as p-methoxyphenol, ethylene glycol, and thiophenol, a protocol has been developed to prepare multigram quantities of the polyfunctionalized cyclohexane (±)-7. A highly efficie
A selective procedure for α-alkenylation of enones involving Pd-catalyzed alkenyl-alkenyl coupling and its application to a convergent and efficient synthesis of nakienone B
Pour, Milan,Negishi, Ei-Ichi
, p. 4679 - 4682 (2007/10/03)
A convergent and efficient synthesis of a marine natural product, nakienone B (1), was achieved using a new protocol for α-alkenylation of enones involving Pd-catalyzed coupling of alkenylzincs with alkenyl iodides. This protocol features (i) avoidance of acidic conditions and (ii) flexibility in charge affinity pattern with respect to the two alkenyl groups to be coupled.
Asymmetrische katalytische Isomerisierung von meso-1,4-Endiolethern mit einem chiralen binap-Rh(I)-Komplex
Hiroya, Kou,Kurihara, Yuko,Ogasawara, Kunio
, p. 2445 - 2448 (2007/10/03)
Keywords: Asymmetrische Synthesen, Isomerisierungen, Katalyse, Rhodiumverbindungen
Total Syntheses of ML-236A and Compactin by Combining the Lactonic (Silyl) Enolate Rearrangement and Aldehyde-Diene Cyclocondensation Technologies
Danishefsky, Samuel J.,Simoneau, Bruno
, p. 2599 - 2604 (2007/10/02)
The sequence of a lactonic Claisen rearrangement and a Lewis acid catalyzed cyclocondensation of an aldehyde with an appropriate diene affords a new route to the title series.
