CH438 Organic Reactions and Synthesis

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

Class: TTh 10:30-12:00

Class Lecture Hall: Building E6-4, room# 2124 (Lectures on the first two weeks will be delivered online at 10:30 am by the Zoom system. 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:     임형근 (Hyeonggeun Lim, rahzell@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, 1st 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)

Exams

    Midterm exam

  • Date: 5/07 (Thr), 2020
  • Time: 09:00 am - 11:45 am.
  • Venue: E6-4 room# 2124
  • Claim Session: TBD

    Final Exam

  • Date: 7/02 (Thr), 2020
  • Time: 09:00 am -11:45 am.
  • Venue: E6-4 room# 2124
  • Claim Session: TBD

Course Schedule

Week

Date

Themes

Contents

1

3/17,19

Introduction

Heterocycle Synthesis

Introduction to the course

Indole/Heterocycles Synthesis I (+ The Art of Drawing Arrow-Pushing Mechanism)

Class will be delivered online at 10:30 am using the Zoom system.

Join the class in the following URL. https://zoom.us/j/4217755535 , Meeting ID: 421-775-5535

2

3/24,26

Heterocycle Synthesis

Heterocycles Synthesis II (+pKa)

Heterocycles Synthesis III

Class will be delivered online at 10:30 am using the Zoom system.

Join the class in the following URL. https://zoom.us/j/4217755535 , Meeting ID: 421-775-5535

3

3/31,4/02

Alkenes Synthesis

Alkenes Synthesis by Elimination Reaction

Stereoselective Alkenes Synthesis by C-C Bond Formation I

4

4/07,09

Alkenes Synthesis

Hydrozirconation

Metal-Catalyzed Cross-Coupling

Stereoselective Alkenes Synthesis by C-C Bond Formation II

Hydrozirconation.

Practical Stille Cross-Coupling.

5

4/14,16

Metal-Catalyzed Cross-Coupling

Practical Suzuki-Miyaura Cross-Coupling.

Practical Metal-Catalyzed Cross-Coupling including Sonogashira, NHTK, Tsuji-Trost Allylation Reactions.

6

4/21,23

Metal-Catalyzed Asymmetric Allylation

Trost Pd-Catalyzed Asymmetric Allylic Alkylation and Carreira Allylation

Named Reactions Involving 1,2-Shift Rearrangement

7

4/28,30

Metal-Halogen Exchange

No Class on 4/30: Budda’s Birthday

Lithium/Magnesium-Halogen Exchange.

8

5/05,07

Midterm Exam

Midterm Exam on 5/07 (Thr) 9 am.

9

5/12,14

Organolithium

Name Reactions Involving Carbanions.

Directed Ortho Lithiation.

10

5/19,21

Organolithium

Organoboron

Stereoselective C-C Bond Formation by Organolithium+Organoboron Chemistry (Aggarwal Chemistry)

11

5/26,28

Olefin Metathesis

Olefin Metathesis

12

6/02,04

Proton Coupled Electron Transfer

Strategies in Organic Synthesis

Proton Coupled Electron Transfer

Strategies in Organic Synthesis I

13

6/09,11

Strategies in Organic Synthesis

Strategies in Organic Synthesis II

Strategies in Organic Synthesis III

14

6/16,18

Metal Catalyzed HAT

 Practical Metal-Hydride-Based Hydrogen Atom Transfer in Organic Synthesis

15

6/23,25

Review Session

 

16

6/30,7/02

Final Exam

Final Exam on 7/02 (Thr) 9 am, this date might subject to change to earlier date upon students’ requests.