CH438 Organic Reactions and Synthesis

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

Class: TTh 10:30-12:00

Class Lecture HallUnless 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, 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)

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.