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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 Spring semester 2017 Seminar Schedule file - -
13 [Thu. 23 Mar. 2017] Prof. Sangsu Bae/Department of Chemistry, Hanyang University, Seoul, South Korea Prof. Sangsu Bae Thu. 23 Mar. 2017
12 [Thu. 30 Mar. 2017] Prof. Jeong Ho Cho/SKKU Advanced Institute of Nanotechnology (SAINT), School of Chemical Engineering, Sungkyunkwan University, Suwon, Korea Prof. Jeong Ho Cho Thu. 30 Mar. 2017
11 [Thu. 6 Apr. 2017] Prof. Rong-Jie Chein/Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan Prof. Rong-Jie Chein Thu. 6 Apr. 2017
10 [Thu. 13 Apr. 2017] Dr. Wan Ki Bae/Photoelectronic Hybrid Research Center, Korea Institute of Science and Technology, Seoul, Korea Dr. Wan Ki Bae Thu. 13 Apr. 2017
9 [Thu. 27 Apr. 2017] Seminar was canceled! - -
8 [Thu. 11 May. 2017] Prof. Andreas Heinrich/IBS Research, Center for Quantum Nanoscience, Seoul, South Korea Prof. Andreas Heinrich Thu. 11 May. 2017
7 [Thu. 18 May. 2017] Student Host Colloquium : 1,1-Bisborylalkane: New Class of Organoboron Compound for the Chemo, Regio and Stereoselective Organic Transformations Prof. Seung Hwan Cho Thu. 18 May. 2017
6 [Thu. 25 May. 2017] Prof. Wonsuk Kim/Department of Chemistry and Nano Science, Ewha Womans University, Seoul Prof. Wonsuk Kim Thu. 25 May. 2017
5 [Thu. 1 Jun. 2017] Prof. Jong-Man Kim/Department of Chemical Engineering, Hanyang University, Seoul, Korea Prof. Jong-Man Kim Thu. 1 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
3 [Fri. 16 Jun. 2017] Prof. Martin Thuo/Department of Materials Science and Engineering, Iowa State University, USA Prof. Martin Thuo Fri. 16 Jun. 2017
2 [Wed. 5 July. 2017] Seminar was canceled! - -
1 7th Jilin-Korea-Waseda Alliance Annual Symposium file - August 17 ~ 19, 2017
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