Asymmetric Organic Synthesis and Drug Synthesis Lab

[135th General Meeting of the Korean Chemical Society; 2025. 04. 23~25, Convention center, Suwon]

Congrats~! Cheong Hoon became a laureate of the "Best Poster" award given by Organic Chemistry Division in the Korean Chemical Society. 

The title is 'Regioselective Formal Hydroamidation of Alkynes: Synthesis of a-Substituted Acrylamides'. This project can be done in collaboration with Seeun Lim at Kwangwoon university under the guidance of Prof. Yunmi Lee. Their synthetic method featured practical preparation of conjugate amides with commercially available alkynes and isocyanates.  Nickel catalyst can control the regioselectivity of hydroalumination of DIBAL-H to terminal alkynes and the subsequent nucleophilic addition of alkenyl-Al intermediates to isocyanates afforded the desired conjugate amides in high yields. 

The endeavor of Cheong Hoon and Seeun for this project also ended up with the publication in European Journal of Organic Chemistry.  

[ACS Catalysis, 25-02-07: Synthesis of (Z)-Allylsilanes by Cu-Catalyzed Regioselective Protosilylation of Allenes via a Single-Electron Process]

Congrats~! Min and Seongha reported their works in ACS Catalysis under the supervision of Prof. Yunmi Lee (KW), Prof. Sangwon Seo and me. 

We developed the Cu-catalytic protocol which enables (Z)-selective formation of linear allylsilanes with a broad range of allenes. In contrast to the previous reports which led to (E)-allylsilanes with Cu catalyst, we chose the different approach to get the opposite forms, namely protosilylation rather than hydrosilylation. For the successful development, the most challenging part was the regioselective silacupuration of Cu-Si intermediate to an allene substrate. We found that silacupration of our system was occurred through a single-electron process due to the congested Cu center, which prohibited conventional 1,2-migratory insertion in other Cu systems. Our method is gram-scalable and tolerable to various kinds of functional groups (FGs), including free alcohol bearing acidic protons. The demonstration of allysilanes' synthetic applications was highlighted the synthetic utility of our protocols. 

[ACS Catalysis, 24-04-05: Ni-Catalyzed Mono- and Dihydrosilylation of Aliphatic Alkynes in Aqueous and Aerobic Conditions]

Congrats~! Chanmi reported her works in ACS Catalysis in collaboration with Prof. Sung You Hong's research group in UNIST. 

We developed the method of preparing 1,1-disilanes from terminal alkynes under aqueous and air conditions. By sequential hydrosilylation with Ph2SiH2 and PhMeSiH2, the chiral center bearing two C-Si bonds can be formed. Experimentally, we proved the existence of Ni(+2) intermediates including LNi(acac)H by XRD and HRMS analysis. Computational studies based on the seminal references revealed that LNi(+1)H would be formed (other forms could not explain the regioselectivity of experimental results at all). Chanmi was super amazing: 1) optimization of mono- and dihydrosilylation of alkynes, 2) screening of substrate scope, 3) control experiments and mechanistic studies, 4) synthetic applications: She did all jobs by herself and finally nailed it!!!  

To Dr. Jaesung Kwak and Prof. Sangwon Seo, I am  deeply grateful for their excellent works for computations. I also appreciate Prof. Wonyoung Choe for XRD analysis. 

[Organic Letters, 23-12-15: Cu-Catalyzed Synthesis of 2-Silyl-1,3-butadienes from Allenols and Applications to One-Pot Synthesis of Tetrasubstituted Arylsilanes]

Congrats~! Yurim and Yeonjoo reported their work in Organic Letters in collaboration with Prof. Yunmi Lee's research group in Kwangwoon University. 

We developed the method of preparing 2-Si-1,3-butadiene analogues from easily accessible allenols in high yields. 2-Si-1,3-dienes, known as versatile dienes for Diels-Alder reactions, indeed are good for Diels-Alder reaction with activated dienophiles. By the combination of Cu-catalyzed silylation, Diels-Alder reaction, and mild oxidation in the single reaction apparatus, we could showcase the synthetic utility by the one-pot synthesis of tetrasubstituted arylsilanes from allenols. 

To Hwiwoong Lee and Telma Kamranifard, as collaborators, we are  deeply grateful for their excellent works under the supervision of Prof. Yunmi Lee.  

[132th General Meeting of the Korean Chemical Society; 2023. 10. 25~27, 김대중컨벤션센터 광주]

Congrats~! Yurim got the "Best Poster" award by Organic Chemistry Division in KCS. 

The title is 'Cu-Catalyzed Regioselective Hydrosilylation of Mono- and Di-substituted Allenes'. This project has been progressed in collaboration with Min Kim.  

We just finished the optimization of reaction conditions. Now, we seek the synthetic applications, especially asymmetric reactions with with allylsilanes.  

[2023(23th)_Summer Workshop_Organic Chemistry Division; 2023. 08. 23~25, 알펜시아 평창]

Congrats~! Yeonjoo got the "Best Presentation" award by Korea Toray Science Foundation. It is awarded to the Top 1 presenter. 

The title is 'Cu-Catalyzed 1,2-Diboration of 1-Substituted Allenols: Mechanistic Aspects and Synthetic Applications' and based on the project published in ACS Catalysis. 

We appreciate Hwiwoong Lee, JuHyung Lee, and Prof. Joongoo Kang for their contribution on this project. 

Finally, we are always grateful to Prof. Yunmi Lee for everything.  

[2023(23th)_Summer Workshop_Organic Chemistry Division; 2023. 08. 23~25, 알펜시아 평창]

Congrats~! Chanmi got the "Best Poster" award. 

The title is 'Regioselective Synthesis of β-Vinylsilanes and Geminal Bis(silanes) from Alkyl-Substituted Alkynes through Solvent-Free or On-Water Catalysis'. 

This project is collaborated with Prof. Sung You Hong's research group in UNIST and Dr. Jaesung Kwak. 

We appreciate Mr. Ji Hwan Jeon for the contributions on mechanistic studies. 

[ACS Catalysis, 23-02-17: Synthesis of α-Borylmethyl-(E)-Allylborons via Cu-Catalyzed Diboration of 1-Substituted Allenols and Their Application in Stereoselective Aldehyde Allylation]

Congrats~! Yeonjoo and Yurim reported their work in ACS Catalysis in collaboration with Prof. Yunmi Lee's research group in Kwangwoon University. We are also grateful for great works of DFT computations by JuHyung Lee under the supervision of Prof. Joongoo Kang in our institute. 

This article includes various sorts of mechanstic aspects as well as synthetic views about preparation and applications of diborons, so we do believe that it should be helpful in fields of organoborons chemistry. 

[130th General Meeting of the Korean Chemical Society; 2022. 10. 19~21, HICO 경주]

Congrats~! Yeonjoo got the "Excellent Poster" award and "Dongwoo FineChem" award. 

The title is 'Cu-Catalyzed Regio- and Stereoselective Diboration of 1-Alkyl or Aryl-substituted-buta-2,3-dien-1-ols'. 

This project is collaborated with Prof. Yunmi Lee's research group in Kwangwoon Univ. and still ongoing. 

I appreciate Mr. Hwiwoong Lee, Ms. Yurim Lee, and Mr. JuHyung Lee for their huge contributions. 

[2022(22th)_Summer Workshop_Organic Chemistry Division; 2022. 08. 24~08.26, 델피노 속초]

Congrats~! Yeonjoo got the "Best Poster" award. 

The title is 'Synthesis of α-Silyl-α,β-unsaturated Amides and Alkynamides from Alkynes with Al-reagents and Isocyanates'. 

This project was collaborated with Prof. Yunmi Lee's research group in Kwangwoon Univ. and reported in J. Org. Chem. (2020, 85, 12024) and Org. Biomol. Chem. (2022, 20, 139). 

I appreciate Mr. Soohong Cho for his great achievements and excellent attitude.