Loading...
2017.11.27 10:22

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

?

Shortcut

PrevPrev Article

NextNext Article

+ - Up Down Comment Print
?

Shortcut

PrevPrev Article

NextNext Article

+ - Up Down Comment Print
Extra Form
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.


  1. [Wed. 5 July. 2017] Seminar is canceled!

    -
    -
    Read More
  2. [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

    Prof. James Y. Hamilton
    Wednesday 28 December 2016
    Read More
  3. [Thu. 9 Mar. 2017] Prof. Woon Ju Song/Department of Chemistry, Seoul National University, Seoul, Korea

    Prof. Woon Ju Song
    Thu. 9 Mar. 2017
    Read More
  4. [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
    Read More
  5. [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
    Read More
  6. [Thu. 8 Jun. 2017] Prof. Won-jin Chung/Department of Chemistry, GIST, Gwangju, Republic of Korea

    Prof. Won-jin Chung
    Thu. 8 Jun. 2017
    Read More
  7. [Thu. 6 Oct. 2016] Prof. Young S. Park/Atomistic Molecular Engineering of Polycyclic Aromatic Hydrocarbons

    Prof. Young S. Park
    Thursday 6 October 2016
    Read More
  8. [Thu. 6 Dec. 2018] Prof. Dong-Ho Kim/Department of Chemistry, Yonsei University, Seoul, Korea

    Prof. Dong-Ho Kim (Yonsei University)
    Thu. 6 Dec. 2018
    Read More
  9. [Thu. 6 Apr. 2017] Prof. Rong-Jie Chein/Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan

    Prof. Rong-Jie Chein
    Thu. 6 Apr. 2017
    Read More
  10. [Thu. 30 Nov. 2017] Prof. Sunmin Ryu/Department of Chemistry, POSTECH, Pohang, South Korea

    Prof. Sunmin Ryu
    Thu. 30 Nov. 2017
    Read More
  11. [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
    Read More
  12. [Thu. 3 Nov. 2016] Prof. Min-Sik Kim/Mass spectrometry and its applications to Biological Discovery

    Prof. Min-Sik Kim
    Thursday 3 November 2016
    Read More
  13. [Thu. 29 Sep. 2016] Prof. Tae-Young Yoon/Observation of Single Membrane Proteins under Mechanical Tension

    Prof. Tae-Young Yoon
    Thursday 29 September 2016
    Read More
  14. [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
    Read More
  15. [Thu. 27 Apr. 2017] Seminar was canceled!

    -
    -
    Read More
  16. [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
    Read More
  17. [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
    Read More
  18. [Thu. 25 May. 2017] Prof. Wonsuk Kim/Department of Chemistry and Nano Science, Ewha Womans University, Seoul

    Prof. Wonsuk Kim
    Thu. 25 May. 2017
    Read More
  19. [Thu. 23 Nov. 2017] Prof. Sung-Gon Kim/Department of Chemistry, Kyonggi University, Suwon, Korea

    Prof. Sung-Gon Kim
    Thu. 23 Nov. 2017
    Read More
  20. [Thu. 23 Mar. 2017] Prof. Sangsu Bae/Department of Chemistry, Hanyang University, Seoul, South Korea

    Prof. Sangsu Bae
    Thu. 23 Mar. 2017
    Read More
Board Pagination ‹ Prev 1 2 3 4 5 6 7 8 Next ›
/ 8

Designed by sketchbooks.co.kr / sketchbook5 board skin

나눔글꼴 설치 안내


이 PC에는 나눔글꼴이 설치되어 있지 않습니다.

이 사이트를 나눔글꼴로 보기 위해서는
나눔글꼴을 설치해야 합니다.

설치 Cancel

Sketchbook5, 스케치북5

Sketchbook5, 스케치북5

Sketchbook5, 스케치북5

Sketchbook5, 스케치북5

Department of Chemistry, Korea University, Tel) +82-2-3290-3120
145 Anam-ro Seongbuk-gu Seoul, 02841, Republic of Korea
Copyright(c) 2014 KOREA UNIVERSITY DEPARTMENT of CHEMISTRY. All right reserved.