|Speaker||Prof. Rong-Jie Chein|
|Date||Thu. 6 Apr. 2017|
|Venue||#633, Asan Hall, College of Science|
“Hydroxy/Amine-Directed Ortho-Alkylation and Its Application
in Total Synthesis of Panduratin D”
Hydroxyl/amine-directed ortho-nucleophilic acyl alkylations of N,N-diethylarylamides have been developed using a simple reagent combination of LDA and chlorosilane. The
transformations involve: 1) a complex-induced proximity effect (CIPE) in the deprotonation step, 2) an intramolecular Peterson-type reaction of the resulting α-silyl carbanion with the amide group, and 3) fission of the final β-oxygenated/nitrogenated silyl intermediate. The study of the mechanism, as well as the application of the protocol to an anionic Hellwinkel-Snieckus-Fries rearrangement, a series of highly efficient functional group transformations, and a total synthesis of Panduratin D, a cytotoxic natural product against pancreatic cancer cells, are reported.
 H.-J. Lo, C.-Y. Lin, M.-C. Tseng, R.-J. Chein, Angew. Chem. Int. Ed. 2014, 53, 9026.
 C.-Y. Lin, M.-C. Tseng, R.-J. Chein, Synlett: SYNPACTS, 2014, 25, 2827–2830.
 I. F. Yu, R.-J. Chein, to be submitted.
 S. R. Bavikar, R.-J. Chein, to be submitted.
“Chiral Tetrahydrothiophene Ligands in Asymmetric Catalysis”
Chiral sulfur ligands are becoming a versatile tool in organic chemistry due to the
blossomed development achieved in the past years. This presentation describes an
expeditious and efficient preparation of enantiopure (thiolan-2-yl)diarylmethanols and
the applications of their derivatives to catalytic and asymmetric Corey-Chaykovsky
epoxidation,1 the imino Corey-Chaykovsky aziridination,2,3 as well as the first oxathiaborenium catalyzed asymmetric Diels-Alder reaction.4,5
1. Wu, H.-Y.; Chang, C.-W.; Chein, R.-J. J. Org. Chem. 2013, 78, 5788-5793.
2. Huang, M.-T.; H.-Y. Wu; Chein, R.-J. Chem. Commun. 2014, 50, 1101-1103.
3. Wang, S.-H.; Chein, R.-J. Tetrahedron, 2016, 72, 2607-2615.
4. Kumar, S. N.; Yu, I. F.; Chein, R.-J. Org. Lett. 2017, 19, 22-25. (Highlighted by C&EN 2017, 95(1), 9).
5. Tsai, M.-L.; Chein, R.-J. to be submitted.
Prof. Rong-Jie Chein
Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan
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|Notice||Fall semester 2017 Seminar Schedule||-||-|
|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||Prof. James Y. Hamilton||Wednesday 28 December 2016|
|48||[October 10, 2017] Novel Terahertz Spectroscopies||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||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|
|»||[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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