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. September 30th (Thu) Graduate School Seminar / Shim Chang-seop Senior Research Fellow

    Shim Chang-seop Senior Research Fellow (Korea Environment Institute)
    Thursday, September 30, 2021
    Read More
  2. September 23rd (Thu) Graduate Seminar / Professor Gregory C. Welch

    September 23rd (Thu) Graduate Seminar / Professor Gregory C. Welch
    Professor Gregory C. Welch (University of Calgary)
    Read More
  3. August 18th (Thu) Graduate School Special Seminar / Seongwon Kim Executive Director

    Seongwon Kim Executive Director (UDC Korea)
    Thursday, August 18, 2022
    Read More
  4. June 16th (Thu) Graduate Seminar / Proffessor Philippe Guyot-Sionnest

    Proffessor Philippe Guyot-Sionnest (The University of Chicago)
    Thursday, June 16, 2022
    Read More
  5. June 3rd (Thursday) Graduate Seminar / Professor Yuseong Chung

    Professor Yuseong Chung (KAIST Department of Biochemical Engineering)
    Thursday, June 3, 2021
    Read More
  6. December 1st (Thu) Professor Park Yun-soo

    Professor Yunsoo Park (KAIST Department of Chemistry)
    Thursday, December 1, 2022
    Read More
  7. May 26th (Thursday) Graduate Seminar / Professor Yunjeong Hwang

    Professor Yunjeong Hwang (Department of Chemistry, Seoul National University)
    Thursday, May 26, 2022
    Read More
  8. November 3rd (Thu) Professor Yunhak Kim

    Professor Yunhak Kim (Busan ​​National University School of Medicine)
    Thursday, November 3, 2022
    Read More
  9. April 13, 2023 (Thu) Professor Baek Yoon-jeong

    Professor Yoonjung Baek (KAIST Department of Chemistry)
    Thursday, April 13, 2023
    Read More
  10. March 25th (Thu) Graduate Seminar / Prof. Yoo Jae-joong

    Professor Yoo Jae-joong (Sungkyunkwan University Department of Physics)
    Thursday, March 25, 2021
    Read More
  11. November 26th (Thursday) Graduate Seminar / Professor Yonghoon Kwon

    Professor Yonghoon Kwon (Department of Applied Biochemistry, Seoul National University)
    November 26, 2020 (Thu)
    Read More
  12. May 6th (Thu) Graduate Seminar / Professor Jeong Yong-chul

    Professor Yongcheol Jeong (Busan ​​National University School of Chemical and Biomolecular Engineering)
    Thursday, May 6, 2021
    Read More
  13. March 30, 2023 (Thursday) Professor Taesoo Choi

    Professor Taesoo Choi (Korea University School of Biological Sciences)
    March 30, 2023 (Thursday)
    Read More
  14. May 13th (Thu) Graduate Seminar / Professor Sunah Park

    Professor Sunah Park (POSTECH Department of Chemistry)
    Thursday, May 13, 2021
    Read More
  15. October 28th (Thu) Graduate Seminar / Professor Simseong Lee

    Professor Simseong Lee (Gyeongsang National University Department of Chemistry)
    Thursday, October 28, 2021
    Read More
  16. May 16, 2023 (Tuesday) Professor Simone Fabiano

    Professor Simone Fabiano (Laboratory of Organic Electronics, Department of Science and Technology, Linköping University )
    May 16, 2023 (Tue)
    Read More
  17. May 4, 2023 (Thursday) Professor Seungyoon Hong

    Professor Seungyoon Hong (Department of Chemistry, Seoul National University)
    Thursday, May 4, 2023
    Read More
  18. October 13 (Thu) Professor Han Seung-woo

    Professor Seungwoo Han (Department of Materials Science and Engineering, Seoul National University)
    Thursday, October 13, 2022
    Read More
  19. April 1st (Thu) Graduate Seminar / Prof. Seonwoo Lee

    Professor Seonwoo Lee (Chonnam National University Department of Chemistry)
    Thursday, April 1, 2021
    Read More
  20. March 11th (Thu) Graduate Seminar / Professor Seongjun Moo

    Professor Seongjun Moo (Chosun University Military Department)
    Thursday, March 11, 2021
    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.