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2017.06.12 15:01

[Thu. 8 Jun. 2017] Prof. Won-jin Chung/Department of Chemistry, GIST, Gwangju, Republic of Korea

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Speaker Prof. Won-jin Chung
Date Thu. 8 Jun. 2017
Time 5:00pm
Venue #633, Asan Hall, College of Science

“Part 1. A Catalytic Enantioselective Glycolate Aldol Reaction

via Lewis Base Activation of Lewis Acids”

 

Part 1. A general, efficient, Lewis-base catalyzed enantioselective addition of glycolate-derived silyl ketene acetals to a wide range of aldehydes will be presented. Both syn- and anti-diastereomers are accessible without changing the catalyst or controlling the geometry of the silyl ketene acetal. Simple modification of the size of alkyl groups on the silyl ketene acetal is sufficient to reverse the stereochemical course of the addition. The observed diastereoselectivity and reactivity could be rationalized by the analysis of six open transition state structures with the aid of computational analysis.

 

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“Part 2. A General Enantioselective Approach to

the Chemical Synthesis of the Chlorosulfolipids”

 

Part 2. A concise and general approach has been developed for the enantioselective synthesis of three structurally related chlorosulfolipids. Key advances include highly stereocontrolled additions to a,b-dichloroaldehydes, kinetic resolution of complex chlorinated vinyl epoxide intermediates, and Z-selective alkene cross metathesis of cis-vinyl epoxides. This strategy facilitated the synthesis of enantioenriched danicalipin A, mytilipin A, and malhamensilipin A in nine, eight, and eleven steps, respectively.

 

2.png

 

 

 

 

References

1. Chung, W.-j.; Carlson, J. S.; Vanderwal, C. D. J. Org. Chem. 2014, 79, 2226–2241.

2. Chung, W.-j.; Vanderwal, C. D. Acc. Chem. Res. 2014, 47, 718–728.

3. Chung, W.-j.; Carlson, J. S.; Bedke, D. K.; Vanderwal, C. D. Angew. Chem. Int. Ed. 2013, 52, 10052–10055.

4. Denmark, S. E.; Chung, W.-j. J. Org. Chem. 2008, 73, 4582–4595.

5. Denmark, S. E.; Chung, W.-j. Angew. Chem. Int. Ed. 2008, 47, 1890–1892.

 

 

Prof. Won-jin Chung
Department of Chemistry, GIST, Gwangju, Republic of Korea


List of Articles
No. Subject Speaker Date
Notice Fall semester 2017 Seminar Schedule file - -
48 [January 24, 2018] Electro-Optic Organic THz Wave Sources file Prof. O-Pil Kwon(Ajou University) January 24, 2018 (Wednesday)
47 [Thu. 30 Nov. 2017] Prof. Sunmin Ryu/Department of Chemistry, POSTECH, Pohang, South Korea Prof. Sunmin Ryu Thu. 30 Nov. 2017
46 [Thu. 23 Nov. 2017] Prof. Sung-Gon Kim/Department of Chemistry, Kyonggi University, Suwon, Korea Prof. Sung-Gon Kim Thu. 23 Nov. 2017
45 [November 14, 2017] Zero-Point Energy, Fluctuations, and Dissipation : A (Mostly) Quantum-Optical Perspective Prof. Milonni, Peter November 14, 2017
44 [Thu. 16 Nov. 2017] Prof. Hyungjun Kim/Department of Chemistry, and Graduate school of Energy, Environment, Water, and Sustainability (EEWS), KAIST, Daejeon, Korea Prof. Hyungjun Kim Thu. 16 Nov. 2017
43 [Fri. 30 Oct. 2017] Prof. Igor Rodin/Department of Chemistry, Moscow State University, Moscow, Russia Prof. Igor Rodin Fri. 30 Oct. 201
42 [October 31, 2017] New ways of vision: Protein structures in translational medicine and business development, my experience file Prof. Robert Huber(1988 Nobel Prize in Chemistry) October 31, 2017
41 [Thu. 26 Oct. 2017] Dr. Jung-Nyoung Heo/Center for Medicinal Chemistry Research, Korea Research Institute of Chemical Technology, Daejeon, Korea Dr. Jung-Nyoung Heo Thu. 26 Oct. 2017
40 [October 25, 2017] Ultrafast electron microscopy: applications in chemical and materials sciences Dr. Byung-Kuk Yoo October 25, 2017
39 [Mon. 16 Oct. 2017] Prof. Kirk S. Schanze/Department of Chemistry, University of Texas at San Antonio, Texas, USA Prof. Kirk S. Schanze Mon. 16 Oct. 2017
38 [Fri. 13 Oct. 2017] Dr. J. Nathan Hohman/The Molecular Foundry, Lawrence Berkeley National Laboratory, California, USA Dr. J. Nathan Hohman Fri. 13 Oct. 2017
37 [Thu. 12 Oct. 2017] Student Host Colloquium : Versatile Dendrimer-Encapsulated Nanoparticles for Analytical Applications Prof. Joohoon Kim Thu. 12 Oct. 2017
36 [October 10, 2017] Novel Terahertz Spectroscopies file Director Mischa Bonn Tue, October 10, 2017
35 [Thu. 28 Sep. 2017] Prof. Eunsung Lee/Department of Chemistry, POSTECH and Center for Self–assembly and Complexity, Institute for Basic Science (IBS), Pohang, Republic of Korea Prof. Eunsung Lee Thu. 28 Sep. 2017
34 [Thu. 14 Sep. 2017] Prof. Dokyoung Kim/Department of Anatomy and Neurobiology, Kyung Hee University, Seoul Prof. Dokyoung Kim Thu. 14 Sep. 2017
33 7th Jilin-Korea-Waseda Alliance Annual Symposium file - August 17 ~ 19, 2017
32 [Wed. 5 July. 2017] Seminar is canceled! - -
31 [Fri. 16 Jun. 2017] Prof. Martin Thuo/Department of Materials Science and Engineering, Iowa State University, USA Prof. Martin Thuo Fri. 16 Jun. 2017
» [Thu. 8 Jun. 2017] Prof. Won-jin Chung/Department of Chemistry, GIST, Gwangju, Republic of Korea Prof. Won-jin Chung Thu. 8 Jun. 2017
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