Rational Design of Highly Diastereoselective, Organic Base-Catalyzed, Room-Temperature Michael Addition Reactions1

2000 ◽  
Vol 65 (20) ◽  
pp. 6688-6696 ◽  
Author(s):  
Vadim A. Soloshonok ◽  
Chaozhong Cai ◽  
Victor J. Hruby ◽  
Luc Van Meervelt ◽  
Takashi Yamazaki
2020 ◽  
Author(s):  
Yunzhong Wang ◽  
Saixing Tang ◽  
Yating Wen ◽  
Shuyuan Zheng ◽  
Bing Yang ◽  
...  

<div>Persistent room-temperature phosphorescence (p-RTP) from pure organics is attractive </div><div>due to its fundamental importance and potential applications in molecular imaging, </div><div>sensing, encryption, anticounterfeiting, etc.1-4 Recently, efforts have been also made in </div><div>obtaining color-tunable p-RTP in aromatic phosphors5 and nonconjugated polymers6,7. </div><div>The origin of color-tunable p-RTP and the rational design of such luminogens, </div><div>particularly those with explicit structure and molecular packing, remain challenging. </div><div>Noteworthily, nonconventional luminophores without significant conjugations generally </div><div>possess excitation-dependent photoluminescence (PL) because of the coexistence of </div><div>diverse clustered chromophores6,8, which strongly implicates the possibility to achieve </div><div>color-tunable p-RTP from their molecular crystals assisted by effective intermolecular </div><div>interactions. Here, inspirited by the highly stable double-helix structure and multiple </div><div>hydrogen bonds in DNA, we reported a series of nonconventional luminophores based on </div><div>hydantoin (HA), which demonstrate excitation-dependent PL and color-tunable p-RTP </div><div>from sky-blue to yellowish-green, accompanying unprecedentedly high PL and p-RTP </div><div>efficiencies of up to 87.5% and 21.8%, respectively. Meanwhile, the p-RTP emissions are </div><div>resistant to vigorous mechanical grinding, with lifetimes of up to 1.74 s. Such robust, </div><div>color-tunable and highly efficient p-RTP render the luminophores promising for varying </div><div>applications. These findings provide mechanism insights into the origin of color-tunable </div><div>p-RTP, and surely advance the exploitation of efficient nonconventional luminophores.</div>


ChemInform ◽  
2003 ◽  
Vol 34 (15) ◽  
Author(s):  
Vadim A. Soloshonok ◽  
Hisanori Ueki ◽  
Changchun Jiang ◽  
Chaozhong Cai ◽  
Victor J. Hruby

RSC Advances ◽  
2015 ◽  
Vol 5 (2) ◽  
pp. 1557-1563 ◽  
Author(s):  
Ruqi Chen ◽  
Jason S. Chen ◽  
Chaoqun Zhang ◽  
Michael R. Kessler

Successful Michael addition under mild reaction conditions resulted in the grafting of 2-methyl aziridine onto acrylated epoxidized soybean oil, and the aziridine content was titrated as 0.00413 mol g−1.


2018 ◽  
Vol 14 ◽  
pp. 3018-3024
Author(s):  
Rudolf Knorr ◽  
Barbara Schmidt

Sterically well-shielded against unsolicited Michael addition and polymerization reactions, α-metalated α-(1,1,3,3-tetramethylindan-2-ylidene)acetonitriles added reversibly to three small aldehydes and two bulky ketones at room temperature. Experimental conditions were determined for transfer of the nucleofugal title carbanion unit between different carbonyl compounds. These readily occurring retro-additions via C–C(O) bond fission may also be used to generate different metal derivatives of the nucleofugal anions as equilibrium components. Fluoride-catalyzed, metal-free desilylation admitted carbonyl addition but blocked the retro-addition.


2019 ◽  
Vol 10 (39) ◽  
pp. 8990-8994 ◽  
Author(s):  
Shan Tang ◽  
David Milstein

Manganese-catalyzed oxa- and aza-Michael addition to unsaturated nitriles was achieved at room temperature under base-free reaction conditions.


2019 ◽  
Vol 55 (18) ◽  
pp. 2668-2671 ◽  
Author(s):  
Xianghui Liu ◽  
Kai Wang ◽  
Wengang Guo ◽  
Yan Liu ◽  
Can Li

Highly enantioselective organocatalytic Michael addition of tritylthiol to N-o-QM intermediates generated in situ at the H2O/DCM interface is presented.


2012 ◽  
Vol 90 (3) ◽  
pp. 290-297 ◽  
Author(s):  
Manoj Kumar Muthyala ◽  
Bhupender S Chhikara ◽  
Keykavous Parang ◽  
Anil Kumar

A novel ionic-liquid-supported 1,5,7-triazabicyclo[4.4.0]dec-5-ene (IL–TBD) was synthesized and investigated for its ability to act as an active organocatalyst in the Michael addition of active methylene compounds and thiophenols to chalcones under solvent-free conditions. The IL–TBD afforded Michael addition products in excellent yields (82%–94%) at room temperature, and it was simply recycled and reused at least five times without significant loss of catalytic activity.


2014 ◽  
Vol 1015 ◽  
pp. 602-605 ◽  
Author(s):  
Hong Ying Zhang ◽  
Xue Ming Yan

A new surfactant-type bifunctional thiourea organocatalysts were synthesized. In the presence of 10 mol% PhCOOH, the Michael reaction of nitroalkenes with various nucleophiles could be catalyzed smoothly by this new organocatalyst in water at room temperature, giving the desired adducts in good yields with high diastereoselectivities (syn/anti=82/18->99/1) and excellent enantioselectivities (up to 97% ee)


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