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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 - -
43 [Thu. 19 May. 2016] Prof. Zhuang Liu/Nanotechnology for enhanced cancer radiation therapy and immunotherapy Prof. Zhuang Liu Thursday 19 May 2016
42 [Thu. 6 Oct. 2016] Prof. Young S. Park/Atomistic Molecular Engineering of Polycyclic Aromatic Hydrocarbons Prof. Young S. Park Thursday 6 October 2016
41 [Thu. 9 Jun. 2016] Prof. Yong-Young Noh/Development of Printed Large Area Organic Transistors and Integrated Circuits Prof. Yong-Young Noh Thursday 9 June 2016
40 [Thu. 9 Mar. 2017] Prof. Woon Ju Song/Department of Chemistry, Seoul National University, Seoul, Korea Prof. Woon Ju Song Thu. 9 Mar. 2017
39 [Thu. 25 May. 2017] Prof. Wonsuk Kim/Department of Chemistry and Nano Science, Ewha Womans University, Seoul Prof. Wonsuk Kim Thu. 25 May. 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
37 [Thu. 29 Sep. 2016] Prof. Tae-Young Yoon/Observation of Single Membrane Proteins under Mechanical Tension Prof. Tae-Young Yoon Thursday 29 September 2016
36 [Thu. 2 Jun. 2016] Prof. Sunkyu Han/Total Syntheses of Complex Alkaloids Inspired by Biosynthetic Hypotheses Prof. Sunkyu Han Thursday 2 June 2016
35 [Mon. 9 Jan. 2017] Prof. Sungwook Woo/Wyss Institute for Biologically Inspired Engineering, Harvard University, USA Prof. Sungwook Woo Mon. 9 Jan. 2017
34 [Thu. 26 Jun. 2016] Prof. Sung June Cho/Structural Elucidation of Novel Zeolite by Dual Space Approaches Using X-ray Powder Diffraction Prof. Sung June Cho Thursday 26 May 2016
33 [Thu. 17 Nov. 2016] Prof. Seunghoon Shin/Synthetic Methods Development based on Rational Analysis of Intermediates file Prof. Seunghoon Shin Thursday 17 November 2016
32 [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
31 [Thu. 23 Mar. 2017] Prof. Sangsu Bae/Department of Chemistry, Hanyang University, Seoul, South Korea Prof. Sangsu Bae Thu. 23 Mar. 2017
30 [Thu. 1 Dec. 2016] Prof. Sang-Yong Ju/Highly Pure Carbon Nanotubes sorted by a Flavin for Thin Film Transistor Applications Prof. Sang-Yong Ju Thursday 1 December 2016
29 [Thu. 6 Apr. 2017] Prof. Rong-Jie Chein/Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan Prof. Rong-Jie Chein Thu. 6 Apr. 2017
28 [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
27 [Thu. 3 Nov. 2016] Prof. Min-Sik Kim/Mass spectrometry and its applications to Biological Discovery Prof. Min-Sik Kim Thursday 3 November 2016
26 [Fri. 16 Jun. 2017] Prof. Martin Thuo/Department of Materials Science and Engineering, Iowa State University, USA Prof. Martin Thuo Fri. 16 Jun. 2017
25 [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
24 [Thu. 12 Oct. 2017] Student Host Colloquium : Versatile Dendrimer-Encapsulated Nanoparticles for Analytical Applications Prof. Joohoon Kim Thu. 12 Oct. 2017
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