54075-10-4Relevant academic research and scientific papers
Asymmetric Catalytic Vinylogous Addition Reactions Initiated by Meinwald Rearrangement of Vinyl Epoxides
Dong, Shunxi,Feng, Xiaoming,He, Jun,Lin, Lili,Song, Yanji,Xu, Jinxiu
supporting information, p. 14521 - 14527 (2021/05/21)
The first catalytic asymmetric multiple vinylogous addition reactions initiated by Meinwald rearrangement of vinyl epoxides were realized by employing chiral N,N′-dioxide/ScIII complex catalysts. The vinyl epoxides, as masked β,γ-unsaturated aldehydes, via direct vinylogous additions with isatins, 2-alkenoylpyridines or methyleneindolinones, provided a facile and efficient way for the synthesis of chiral 3-hydroxy-3-substituted oxindoles, α,β-unsaturated aldehydes and spiro-cyclohexene indolinones, respectively with high efficiency and stereoselectivity. The control experiments and kinetic studies revealed that the Lewis acid acted as dual-tasking catalyst, controlling the initial rearrangement to match subsequent enantioselective vinylogous addition reactions. A catalytic cycle with a possible transition model was proposed to illustrate the reaction mechanism.
Rhodium-Catalyzed Regioselective Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes Using Formic Acid
Fan, Chao,Hou, Jing,Chen, Yu-Jia,Ding, Kui-Ling,Zhou, Qi-Lin
supporting information, p. 2074 - 2077 (2021/04/05)
A rhodium-catalyzed hydroformylation of alkynes with formic acid was developed. The method provides α,β-unsaturated aldehydes in high yield and E-selectivity without the need to handle toxic CO gas.
Mixtures having improved cooling effect
-
Page/Page column 28, (2017/09/15)
A mixtures which contain (a) at least one phenylalkenal of formula (I) wherein R1 and R2 independently represent hydrogen, a methyl or phenyl group, R3 represents hydrogen, a phenyl group, alkenyl group or a linear or branched alkyl group with 1 to 5 carbon atoms, and the broken double lines independently represent a single bond or a double bond, and (b) at least one physiological cooling agent.
Selective rhodium-catalyzed hydroformylation of alkynes to α,β-unsaturated aldehydes with a tetraphosphoramidite ligand
Zhang, Zongpeng,Wang, Qian,Chen, Caiyou,Han, Zhengyu,Dong, Xiu-Qin,Zhang, Xumu
supporting information, p. 3290 - 3293 (2016/07/13)
A tetraphosphoramidite ligand was successfully applied to a Rh-catalyzed hydroformylation of various symmetrical and unsymmetrical alkynes to afford corresponding α,β-unsaturated aldehyde products in good to excellent yields (up to 97% yield). Excellent chemo- and regioselectivities and high activities (up to 20 000 TON) were achieved. The corresponding α,β-unsaturated aldehyde products can be transformed into many useful and important organic molecules, such as indenamine derivatives and lukianol pyrroles. This great performance makes the hydroformylation of alkynes highly practical with great potential.
Selective palladium-catalyzed hydroformylation of alkynes to α,β-Unsaturated Aldehydes
Fang, Xianjie,Zhang, Min,Jackstell, Ralf,Beller, Matthias
, p. 4645 - 4649 (2013/05/22)
Atom-efficient: A selective palladium catalyst system is used for the hydroformylation of alkynes (see picture). In this syngas reaction, various alkynes were smoothly transformed to synthetically interesting α,β-unsaturated aldehydes in good yields with high regio- and stereoselectivity. Copyright
Palladium-catalysed Heck reaction on 1,2-dien-1-ols: a stereoselective synthesis of α-arylated α,β-unsaturated aldehydes
Deagostino, Annamaria,Prandi, Cristina,Toppino, Antonio,Venturello, Paolo
, p. 10344 - 10349 (2008/12/22)
A new methodology for preparing α-arylated α,β-unsaturated aldehydes is reported. The starting materials are all commercially available alkyn-1-ols (1a-c) that have been easily isomerised to the corresponding allenes (2a-c). The key step is the Heck coupling of the 1,2-dien-1-ols with a series of iodo- and bromoarene. The products have been synthesised in good yields, and the reactions were carried out under very mild conditions.
Lewis acid-catalyzed tandem Diels-Alder reaction/retro-Claisen rearrangement as an equivalent of the inverse electron demand hetero Diels-Alder reaction
Davies, Huw M. L.,Dai, Xing
, p. 6680 - 6684 (2007/10/03)
A highly stereoselective formal inverse electron demand hetero Diels-Alder reaction (HDA) occurs on reaction of 2-aryl-α,β-unsaturated aldehydes with cyclopentadiene. The major pathway for this transformation is shown to be a Lewis acid-catalyzed tandem Diels-Alder reaction/retro-Claisen rearrangement.
Phosphine Catalyzed α-Arylation of Enones and Enals Using Hypervalent Bismuth Reagents: Regiospecific Enolate Arylation via Nucleophilic Catalysis
Koech, Phillip K.,Krische, Michael J.
, p. 5350 - 5351 (2007/10/03)
Exposure of enones and enals to 20 mol % tributylphosphine in the presence of triarylbismuth(V) dichlorides results in regiospecific aryl transfer to the α-position of the enone or enal pronucleophile. These results represent the first examples of enolate
Cytochrome P450-catalyzed hydroxylation of mechanistic probes that distinguish between radicals and cations. Evidence for cationic but not for radical intermediates
Newcomb, Martin,Shen, Runnan,Choi, Seung-Yong,Toy, Patrick H.,Hollenberg, Paul F.,Vaz, Alfin D. N.,Coon, Minor J.
, p. 2677 - 2686 (2007/10/03)
Oxidation of the mechanistic probes trans,trans-2-methoxy-3- phenylmethylcyclopropane and methylcubane by six cytochrome P450 isozymes has been studied. The probes differentiate between radical and cationic species in that different structural rearrangeme
