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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 - -
9 [October 25, 2017] Ultrafast electron microscopy: applications in chemical and materials sciences Dr. Byung-Kuk Yoo October 25, 2017
8 [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
7 [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
6 [Fri. 30 Oct. 2017] Prof. Igor Rodin/Department of Chemistry, Moscow State University, Moscow, Russia Prof. Igor Rodin Fri. 30 Oct. 201
5 [Thu. 16 Nov. 2017] Prof. Hyungjun Kim/Department of Chemistry, and Graduate school of Energy, Environment, Water, and Sustainability (EEWS), KAIST, Daejeon, Korea Prof. Hyungjun Kim Thu. 16 Nov. 2017
4 [November 14, 2017] Zero-Point Energy, Fluctuations, and Dissipation : A (Mostly) Quantum-Optical Perspective Prof. Milonni, Peter November 14, 2017
» [Thu. 23 Nov. 2017] Prof. Sung-Gon Kim/Department of Chemistry, Kyonggi University, Suwon, Korea Prof. Sung-Gon Kim Thu. 23 Nov. 2017
2 [Thu. 30 Nov. 2017] Prof. Sunmin Ryu/Department of Chemistry, POSTECH, Pohang, South Korea Prof. Sunmin Ryu Thu. 30 Nov. 2017
1 [January 24, 2018] Electro-Optic Organic THz Wave Sources file Prof. O-Pil Kwon(Ajou University) January 24, 2018 (Wednesday)
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