76594-52-0Relevant academic research and scientific papers
Relay Catalysis to Synthesize β-Substituted Enones: Organocatalytic Substitution of Vinylogous Esters and Amides with Organoboronates
Sundstrom, Sasha,Nguyen, Thien S.,May, Jeremy A.
supporting information, p. 1355 - 1359 (2020/02/13)
Organocatalysis was shown to facilitate conjugate additions to vinylogous esters and amides for the first time. Subsequent elimination of a β-alcohol or amine provided π-conjugated β-substituted enones. Remarkably, nucleophile addition to the electron-rich vinylogous substrates is more rapid than classical enones, forming monosubstituted products. A doubly organocatalytic (organic diol and methyl aniline) conjugate addition synthesized the products directly from alkynyl ketones. Both of these catalytic transformations are orthogonal to transition metal catalysis, allowing for good yields, easily accessible or commercially available reagents, high selectivity, reagent recovery and recyclability, facile scalability, and exceptional functional group tolerance.
Ru-Catalyzed Chemo- And Enantioselective Hydrogenation of 2,4-Pentadien-1-ones: Synthesis of Chiral 2,4-Pentadien-1-ols
Li, Chengyang,Lu, Wenkui,Lu, Bin,Li, Wanfang,Xie, Xiaomin,Zhang, Zhaoguo
, p. 16086 - 16094 (2019/12/24)
The asymmetric hydrogenation of 2,4-pentadien-1-ones has been achieved by using trans-RuCl2[(R)-XylylSunPhos][(R)-Daipen] as a catalyst under basic conditions. This hydrogenation demonstrated exclusive C1-carbonyl selectivity, and thus the conjugated 2,4-diene motifs remained untouched, which provides a synthetically useful method for various chiral 2,4-pentadien-1-ols.
Construction of β to carbonyl stereogenic centres by asymmetric 1,4-addition of alkylzirconocenes to dienones and ynenones
Gao, Zhenbo,Fletcher, Stephen P.
supporting information, p. 3601 - 3604 (2018/04/12)
Copper-catalyzed asymmetric 1,4-addition of alkylzirconium species to linear α,β,γ,δ unsaturated dienones and ynenones is reported. A variety of alkyl nucleophiles are introduced with good yields and excellent regio- and enantio-selectivities to give tertiary carbon centres bearing multiple functional groups. The method is also applicable to an ynethioate with ee's over 96%.
Regio- and Enantioselective Copper-Catalyzed 1,4-Conjugate Addition of Trimethylaluminium to Linear α,β,γ,δ-Unsaturated Alkyl Ketones
Wu, Xiaoting,Xie, Fang,Ling, Zheng,Tang, Liang,Zhang, Wanbin
supporting information, p. 2510 - 2518 (2016/08/16)
A regio- and enantioselective copper-catalyzed 1,4-conjugate addition of trimethylaluminium to linear δ-aryl-substituted α,β,γ,δ-unsaturated alkyl ketones was developed. A series of γ,δ-unsaturated alkyl ketones were obtained in good yields with high regio- and enantioselectivity (up to 88% ee and 96:4 dr). Expansion of the reaction scope to substrates containing aromatic heterocycles also afforded good yields and enantioselectivities (up to 91% ee) with very high regioselectivities, exclusively providing the single 1,4-products. (Figure presented.).
Palladium-catalyzed dienylations of chelated enolates
Basak, Sankar,Kazmaier, Uli
supporting information; experimental part, p. 4169 - 4177 (2009/05/30)
Isomerization-free reactions of dienyl carbonates with chelated amino acid ester enolates at -78 °C provide important information concerning the mechanism of these dienylations. The formation of regioisomeric products can be explained by competing SN2/SN2′ reactions, and the product distribution can be influenced by the proper choice of the reaction conditions. Chiral allylic substrates show a significant transfer of chirality. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Unsaturated Oximes, XXIV: 6-Phenyl-3,5-hexadien-2-ones, 7-Phenyl-4,6-heptadien-3-ones and Their Oximes
Unterhalt, Bernard,Weyrich, Klaus
, p. 913 - 918 (2007/10/02)
Substituted cinnamyl aldehydes are condensed with acetone and butanone.The structures of the resulting unsaturated ketones and their oximes are discussed.
