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2017.11.27 10:22

[Thu. 23 Nov. 2017] Prof. Sung-Gon Kim/Department of Chemistry, Kyonggi University, Suwon, Korea

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Speaker Prof. Sung-Gon Kim
Date Thu. 23 Nov. 2017
Time 5:00pm
Venue #331, Asan Hall, College of Science

 “Organocatalytic Cascade Reactions for the Asymmetric Synthesis 

of Fused-ring Compounds”

 

 

Fused-ring structural units including chroman, indoline, pyrrolidine and hydroqunoline are widely distributed in nature and many biologically active compounds. Molecules containing these structural units exhibit a broad range of bioactivities such as anticancer, antiviral, antitumar, antimicrobial, sex pheromone, and central nervous system activity. Owing to the importance of these class of compounds, the stereoselective synthesis of fused-ring compounds is a noteworthy synthetic goal. In this presentation, we demonstrate the asymmetric synthesis of hydroquinoline, hydroquinazoline, and indolines via catalytic cascade reaction.

First, A synthetic method for the construction of fully substituted enantioenriched 1,4-dihydroquinolines using an organocatalytic aza-Michael/Michael cascade reaction has been developed (Sheme 1). 1 The asymmetric reaction of 2-(tosylamino)phenyl α,β-unsaturated ketones with alkynyl aldehydes, promoted by diphenylprolinol O-TMS ether as an organocatalyst, generated chiral 1,4-dihydroquinolines in good to high yields with excellent enantioselectivities (up to  97% ee)

1.JPG

 

 

 

We have also found a concise synthetic route to valuable highly functionalized benzosulfamidate-fused tetrahydroquinazoline (Scheme 2).2 The [4+2] cycloaddition of o-N-Cbz-amino-b-nitrostyrene with benzoxathiazine 2,2-dioxide using an imidazole as the catalyst afforded tetrahydroquinazolines with high diastereoselectivities. 

 

 

2.JPG

 

 

In addition, we have established the synthesis of chiral benzosulfamidate-fused pyrrolidines through an Mannich/aza-Michael cascade reaction of δ-formyl-a,b-unsaturated ketones with cyclic N-sulfimines (Scheme 3).This simple domino process afforded diverse highly functionalized pyrrolidines in good yields with high diastero- and enantioselectivities.

 3.JPG

 

 

 

 Reference

 

1. Lee, Y.; Heo, S.; Kim, S.-G. Adv. Synth. Catal. 2015357, 1545-1550.

2. Sim, J.-T.; Kim, H. Kim, S.-G. Tetrahedron Lett201657, 5907-5910.

3. Kim, H.; Kim, Y.; Kim, S.-G. J. Org. Chem201782, 8179-8185.


List of Articles
No. Subject Speaker Date
Notice Fall semester 2017 Seminar Schedule file - -
49 [Wed. 28 Dec. 2016] Prof. James Y. Hamilton/Development of a Broad Range of Asymmetric C–C Bond Forming Reactions with a Versatile Iridium Catalyst file Prof. James Y. Hamilton Wednesday 28 December 2016
48 [October 10, 2017] Novel Terahertz Spectroscopies file Director Mischa Bonn Tue, October 10, 2017
47 [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
46 [Thu. 8 Sep. 2016] Prof. Jaeyoung Sung/Stochastic chemical dynamics in living cells and its consequence for the control capacity of living cells over biological functions Prof. Jaeyoung Sung Thursday 8 September 2016
45 [Thu. 6 Oct. 2016] Prof. Young S. Park/Atomistic Molecular Engineering of Polycyclic Aromatic Hydrocarbons Prof. Young S. Park Thursday 6 October 2016
44 [Thu. 3 Nov. 2016] Prof. Min-Sik Kim/Mass spectrometry and its applications to Biological Discovery Prof. Min-Sik Kim Thursday 3 November 2016
43 [Thu. 29 Sep. 2016] Prof. Tae-Young Yoon/Observation of Single Membrane Proteins under Mechanical Tension Prof. Tae-Young Yoon Thursday 29 September 2016
42 [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
41 [Thu. 22 Sep. 2016] Prof. Anna Lee/Organocatalyzed Asymmetric Reactions Prof. Anna Lee Thursday 22 September 2016
40 [Thu. 20 Oct. 2016] Prof. Chan Hyuk Kim/Novel Small Molecule-based Approaches for Cancer Immunotherapy Prof. Chan Hyuk Kim Thursday 20 October 2016
39 [Thu. 2 Jun. 2016] Prof. Sunkyu Han/Total Syntheses of Complex Alkaloids Inspired by Biosynthetic Hypotheses Prof. Sunkyu Han Thursday 2 June 2016
38 [Thu. 19 May. 2016] Prof. Zhuang Liu/Nanotechnology for enhanced cancer radiation therapy and immunotherapy Prof. Zhuang Liu Thursday 19 May 2016
37 [Thu. 17 Nov. 2016] Prof. Seunghoon Shin/Synthetic Methods Development based on Rational Analysis of Intermediates file Prof. Seunghoon Shin Thursday 17 November 2016
36 [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
35 [Thu. 9 Mar. 2017] Prof. Woon Ju Song/Department of Chemistry, Seoul National University, Seoul, Korea Prof. Woon Ju Song Thu. 9 Mar. 2017
34 [Thu. 8 Jun. 2017] Prof. Won-jin Chung/Department of Chemistry, GIST, Gwangju, Republic of Korea Prof. Won-jin Chung Thu. 8 Jun. 2017
33 [Thu. 6 Apr. 2017] Prof. Rong-Jie Chein/Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan Prof. Rong-Jie Chein Thu. 6 Apr. 2017
32 [Thu. 30 Nov. 2017] Prof. Sunmin Ryu/Department of Chemistry, POSTECH, Pohang, South Korea Prof. Sunmin Ryu Thu. 30 Nov. 2017
31 [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
30 [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
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