CH438 Organic Reactions and Synthesis

Instructors: 한순규 (Sunkyu Han, sunkyu.han@kaist.ac.kr)

Class: TTh 10:30-12:00

Class Lecture Hall: Unless otherwise noted, lectures will be delivered online at 10:30 am via Zoom. https://zoom.us/j/4217755535 , Meeting ID: 421-775-5535

Website: synthesis.kaist.ac.kr/orgreactsyn

Office Hours: Mon 14:30~16:00, Wed 14:30~16:00

Teaching Assistant: 이진우 (Jinwoo Lee, jinwoo9524@kaist.ac.kr)

Course Prerequisites:

Organic Chemistry I (CH221), Organic Chemistry II (CH223), Bioorganic Chemistry (CH325), Physical Organic Chemistry (CH336, encouraged)

Course Description:

- Important topics in organic chemistry will be discussed in depth with a spectrum ranging from classical examples to the state of the art cases.

- This course discusses representative name reactions, their mechanism, and synthetic applications in organic chemistry.

- This course is designed to be complementary to other organic chemistry courses such as Organometallic Chemistry (CH542), Organic Synthesis I (CH522), and Organic Synthesis II (CH523). In other words, pericyclic reactions and carbonyl chemistry (1,2 and 1,4 addition, stereochemistry) won’t be discussed in details in this course.

- Details in drawing arrow-pushing mechanisms, heterocycles syntheses, detailed olefin synthesis methods, various olefin functionalizations, practical metal catalyzed cross-coupling reactions, metal catalyzed allylations, organolithium chemistry, Aggarwal chemistry, olefin metathesis, radical chemistry, strategies in complex molecules synthesis will be discussed.

Textbook:

- Strategic Applications of Named Reactions in Organic Synthesis, 1^st Edition, by Laszlo Kurti and Barbara Czako

Supplementary Resources:

- Andrew G. Myers Chemistry 115Handouts (Harvard University)

- Phil Baran Group Seminar Lecture (The Scripps ResearchInstitute)

- David MacMillan Group Seminar Presentation(Princeton University)

- Noah Burns Group Meetings (StanfordUniversity)

- Ryan Shenvi Group Seminars (The Scripps ResearchInstitute)

- Fukuyama Group Meeting Problems (The University of Tokyo)

- Alison Frontier Not Voodoo (University of Rochester)

- Jon Njardarson Top-SellingPharmaceuticals (University of Arizona)

- Jon Njardarson Chemistry by Design (University of Arizona)

- Brian Stoltz Group Literature Seminars (Caltech)

- Allthings Metathesis (Umicore)

- Elizabeth Jarvo Chem 125 Advanced Organic Chemistry (UC Irvine)

- M. Christina White Organometallics Lecture Note (UIUC)

- Eric Ferreira Group Seminars (University of Georgia)

- James Morken Group Presentations (Boston College)

Lecture Slides

Grading Policy

Course Participation: 10

Midterm Exam: 40

Final Exam: 50 (cumulative with an emphasis on the second half of the course)

Extra Point: 10 (Synthesis Target Presentation, 6 students)

Exams

Midterm exam

Date: April 22 (Thr)
Time: 09:00 am -12:00 pm
Venue: TBA
Claim Session: TBD

Final Exam

Date: June 17 (Thr)
Time: 09:00 am -12:00 pm
Venue: TBA
Claim Session: TBD

Course Schedule

Week	Date	Themes	Contents
1	03/02,04	Introduction Heterocycle Synthesis	Introduction to the course Indole/Heterocycles Synthesis I (+ The Art of Drawing Arrow-Pushing Mechanism)
2	03/09,11	Heterocycle Synthesis	Heterocycles Synthesis II (+pKa) Heterocycles Synthesis III
3	03/16,18	Alkenes Synthesis	Alkenes Synthesis by Elimination Reaction Stereoselective Alkenes Synthesis by C-C Bond Formation I
4	03/23,25	Alkenes Synthesis Hydrozirconation Metal-Catalyzed Cross-Coupling	Stereoselective Alkenes Synthesis by C-C Bond Formation II Hydrozirconation. Practical Stille Cross-Coupling.
5	03/20, 04/01	Metal-Catalyzed Cross-Coupling	Practical Suzuki-Miyaura Cross-Coupling. Practical Metal-Catalyzed Cross-Coupling including Sonogashira, NHTK, Tsuji-Trost Allylation Reactions.
6	04/06,08	Metal-Catalyzed Asymmetric Allylation	Trost Pd-Catalyzed Asymmetric Allylic Alkylation and Carreira Allylation Named Reactions Involving 1,2-Shift Rearrangement
7	04/13,15	No class	Prepare for the midterm exam.
8	04/20,22	Midterm Exam	Midterm Exam on April 22 (Thr) 9 am.
9	04/27,29	Metal-Halogen Exchange	Lithium/Magnesium-Halogen Exchange.
10	05/04,06	Organolithium	Name Reactions Involving Carbanions. Directed Ortho Lithiation.
11	05/11,13	Organolithium Organoboron	Stereoselective C-C Bond Formation by Organolithium+Organoboron Chemistry (Aggarwal Chemistry)
12	05/18,20	Olefin Metathesis	Olefin Metathesis
13	05/25,27	Radical Chemistry	Proton Coupled Electron Transfer Metal Hydride-Based Hydrogen Atom Transfer
14	06/01,03	Strategies in Organic Synthesis	Strategies in Organic Synthesis I Strategies in Organic Synthesis II
15	06/08,10	Synthesis Target Presentation	Proposed synthesis of natural products
16	06/15,17	Final Exam	Final Exam on June 17 (Thr) 9 am.