115240-90-9Relevant academic research and scientific papers
Highly Diastereoselective Coupling Reactions between Chiral Benzaldehyde Tricarbonylchromium Complexes and Activated Double Bonds
Kuendig, E. Peter,Xu, Long He,Romanens, Patrick,Bernardinelli, Gerald
, p. 7049 - 7052 (1993)
The amine catalyzed coupling reaction of acrylic derivatives with benzaldehydes (Baylis-Hillman reaction) is more efficient when the arene is complexed to the electrophilic Cr(CO)3 group.Reactions with planar chiral o-substituted benzaldehyde complexes ar
Acceleration of the DABCO-promoted Baylis-Hillman reaction using a recoverable H-bonding organocatalyst
Maher, Declan J.,Connon, Stephen J.
, p. 1301 - 1305 (2004)
It has been shown that catalytic amounts (20-40mol%) of bis-aryl (thio)ureas greatly accelerate the DABCO-promoted Baylis-Hillman reaction between a range of aromatic aldehydes and methyl acrylate in the absence of solvent. These robust organocatalysts ar
Baylis-Hillman reaction in [bdmim][PF6] ionic liquid
Hsu, Jen-Chuah,Yen, Ya-Hew,Chu, Yen-Ho
, p. 4673 - 4676 (2004)
A new use of ionic liquid [bdmim][PF6] as solvent for the Baylis-Hillman reaction is presented. Unlike the commonly used [bmim][PF 6] that evidently reacts with electrophilic aldehydes under basic conditions, ionic liquid [bdmim][PF
Reductive dehydroxylation of Baylis-Hillman adducts with low-valent titanium reagent: Syntheses of stereoselective trisubstituted alkenes
Shadakshari, Uma,Nayak, Sandip K.
, p. 4599 - 4602 (2001)
The Baylis-Hillman adducts prepared from aromatic aldehydes and methyl acrylate underwent smooth dehydroxylation with concomitant olefin isomerisation with low-valent titanium reagent to provide the trisubstituted alkenes with high (E)-selectivity.
Activated Self-Resolution and Error-Correction in Catalytic Reaction Networks**
Schaufelberger, Fredrik,Ramstr?m, Olof
supporting information, p. 10335 - 10340 (2021/05/07)
Understanding the emergence of function in complex reaction networks is a primary goal of systems chemistry and origin-of-life studies. Especially challenging is to create systems that simultaneously exhibit several emergent functions that can be independently tuned. In this work, a multifunctional complex reaction network of nucleophilic small molecule catalysts for the Morita-Baylis-Hillman (MBH) reaction is demonstrated. The dynamic system exhibited triggered self-resolution, preferentially amplifying a specific catalyst/product set out of a many potential alternatives. By utilizing selective reversibility of the products of the reaction set, systemic thermodynamically driven error-correction could also be introduced. To achieve this, a dynamic covalent MBH reaction based on adducts with internal H-transfer capabilities was developed. By careful tuning of the substituents, rate accelerations of retro-MBH reactions of up to four orders of magnitude could be obtained. This study thus demonstrates how efficient self-sorting of catalytic systems can be achieved through an interplay of several complex emergent functionalities.
Kinetic Self-Sorting of Dynamic Covalent Catalysts with Systemic Feedback Regulation
Schaufelberger, Fredrik,Ramstr?m, Olof
supporting information, p. 7836 - 7839 (2016/07/07)
Constructing small molecule systems that mimic the functionality exhibited in biological reaction networks is a key objective of systems chemistry. Herein, we report the development of a dynamic catalytic system where the catalyst activity is modulated through a dynamic covalent bond. By connecting a thermodynamically controlled rearrangement process to resolution under kinetic control, the catalyst system underwent kinetic self-sorting, resulting in amplification of a more reactive catalyst while establishing a catalytic feedback mechanism. The dynamic catalyst system furthermore responded to catalytic events by self-perturbation to regulate its own activity, which in the case of upregulation gave rise to systemic autocatalytic behavior.
Synthesis of Chiral α-Trifluoromethylamines with 2,2,2-Trifluoroethylamine as a "building Block"
Li, Xiaoyuan,Su, Jinhuan,Liu, Zhourujun,Zhu, Yuanyuan,Dong, Zhenghao,Qiu, Shuai,Wang, Jiayi,Lin, Li,Shen, Zhiqiang,Yan, Wenjin,Wang, Kairong,Wang, Rui
supporting information, p. 956 - 959 (2016/03/15)
The β-isocupreidine, a cinchonine derived alkaloid, catalyzed asymmetric SN2′-SN2′ reaction between N-2,2,2-trifluoroethylisatin ketimines and MBH type carbonates was realized in a simple and efficient way. A series of chiral α-trifl
Synthesis and NMR binding studies towards rational design of a series of electron-withdrawing diamide receptors/organocatalysts
Kinsella, Michael,Duggan, Patrick G.,Muldoon, Jimmy,Eccles, Kevin S.,Lawrence, Simon E.,Lennon, Claire M.
supporting information; experimental part, p. 1125 - 1132 (2011/04/15)
A related series of bisamides have been evaluated for rational correlation between anion complexation and organocatalysis: remarkable enhancement of hydrogen bonding to anions was observed along with significant increases in catalytic activity in the Bayl
Nonenzymatic acylative kinetic resolution of Baylis-Hillman adducts
O Dalaigh, Ciaran,Connon, Stephen J.
, p. 7066 - 7069 (2008/02/11)
(Chemical Equation Presented) The first efficient nonenzymatic acylative kinetic resolution of Baylis-Hillman adducts is reported. Chiral pyridine catalyst 1a and an optimized analogue 1e are capable of promoting the synthetically useful enantioselective
Rhodium-catalyzed enantioselective hydrogenation of β-phthalimide acrylates to synthesis of β2-amino acids
Huang, Hanmin,Liu, Xiongcai,Deng, Jun,Qiu, Min,Zheng, Zhuo
, p. 3359 - 3362 (2007/10/03)
The enantioselective hydrogenation of β-phthalimide acrylates provides the corresponding chiral β2-amino acids in excellent enantiomeric excess catalyzed by Rh-monophosphorus.
