Lectures and Reading Assignments
Syllabus
Synthetic Organic Chemistry I is the first semester of our new, unified two-semester introduction to the design of syntheses of complex organic molecules. The focus of the fall semester will be on carbon-carbon bond-forming reactions revolving around the carbonyl group. The course will comprise six units (indicated number of lectures for each unit is tentative):
Unit 1 - Introduction to Strategies for the Synthesis of Complex Molecules (4 lectures) General principles of retrosynthetic analysis and general strategies for stereochemical control. Brief introduction to the Diels-Alder reaction. Discussion of chirality transfer and [3,3] sigmatropic rearrangements.
Unit 2 - Carbanionic Synthons (3 lectures)
Overview of the generation and chemistry of "carbanionic" synthetic building blocks, including enolates, azaenolates, organophosphorus compounds, and organosulfur derivatives. Directed metalation for the generation of aryllithium compounds, and discussion of alkenyl and alkynylmetal compounds. Synthetic applications of “unactivated” organolithium, magnesium, zinc, copper, and palladium species.
Unit 3 - Alkylation and Related Electrophilic Substitution Reactions (4 lectures)
Alkylation of "carbanionic" synthons with alkyl halides, sulfonates, and related electrophilic substitution reactions. Emphasis on stereocontrolled alkylation in acyclic systems.
Unit 4 - 1,2-Addition to Carbonyl Groups (3 lectures)
Stereocontrol elements in 1,2-additions to carbonyl compounds. Stereocontrolled reduction of ketones and 1,2-addition of organometallic compounds to carbonyl groups.
Unit 5 - 1,2 Addition of Allylmetal Compounds to Carbonyl Groups (3 lectures)
Introduction to reactions of carbocationic synthons with carbon-carbon pi bonds including organosilanes and stannanes. Stereocontrolled 1,2-addition of allylboron, titanium, silicon, and tin compounds to carbonyl groups.
Unit 6 - The Aldol Reaction (3 lectures)
Intramolecular aldol reactions including the Robinson annulation. Emphasis on stereocontrolled aldol reactions in acyclic systems.
Functional Group Transformations including reduction, oxidation, and functional group interconversions by nucleophilic substitution, and protective group chemistry, will be covered via a reading assignment in September and practice problems provided during the first few weeks of the course.
Synthetic Organic Chemistry II, taught in the spring semester by Professor Movassaghi, will focus on carbon-nitrogen bond forming reactions and carbon-carbon bond-forming reactions revolving around activated and unactivated alkenes and alkynes. Topics may include conjugate addition, the Michael and Heck reactions, olefin metathesis, the Mannich and Strecker reactions and other 1,2-additions to imine derivatives, and cycloaddition strategies.
Please note that this schedule is tentative and may change during the course of the semester
Lecture |
Date |
Topic |
Notes |
Readings |
| 00 | 09/24 |
Functional Group Transformations |
||
| 01 | 10/03 |
Strategies for Synthesis I |
C&S 13.1 |
|
| 02 | 10/05 |
Strategies for Synthesis II |
C&S 6.1.1 - 6.1.4 |
|
| 03 | 10/10 |
Strategies for Synthesis III |
G&A 1 |
|
| 04 | 10/12 |
Strategies for Synthesis IV |
C&S 6.4 | |
| 05 | 10/17 | Carbanionic Synthons I |
C&S 1, 7.1, 7.2, 7.3.1, 8.1 |
|
| 06 | 10/19 |
Carbanionic Synthons II |
C&S 1, 7.1, 7.2, 7.3.1, 8.1 |
|
| 07 | 10/24 |
Carbanionic Synthons III |
C&S 1, 7.1, 7.2, 7.3.1, 8.1 |
|
| 08 | 10/26 |
Stereocontrolled Alkylation I | G&A 3, 8.4, O'L 2, 3, 29 |
|
| 09 | 10/31 |
Stereocontrolled Alkylation II
|
G&A 3, 8.4, O'L 2, 3, 29 |
|
| 10 | 11/02 |
Stereocontrolled Alkylation III |
G&A 3, 8.4, O'L 2, 3, 29 |
|
| 11 | 11/07 |
Stereocontrolled Alkylation IV |
G&A 3, 8.4, O'L 2, 3, 29 |
|
| 12 | 11/09 | Stereocontrolled Addition to Carbonyls I |
G&A 4.1-4.2, O'L 7 |
|
| 13 | 11/14 |
Stereocontrolled Addition to Carbonyls II |
G&A 7.1, O'L 22, C&S 5.1-5.3 |
|
| 14 | 11/16 |
Stereocontrolled Addition to Carbonyls III | G&A 4.3, O'L 8, C&S 7.3 | |
| 15 | 11/21 |
Addition of Allylmetals to Carbonyls I |
C&S 9.1.1, 9.1.5, 9.2.1-9.2.3, 9.2.6, 9.3.1-9.3.2, 9.4 |
|
| 16 | 11/28 |
Addition of Allylmetal to Carbonyls II |
G&A 5.1; O'L 11 |
|
| 17 | 11/30 |
Addition of Allylmetals to Carbonyls III |
G&A 5.1; O'L 11 |
|
| 18 | 12/05 |
Stereocontrolled Aldol Reactions I |
C&S 2.1 |
|
| 19 | 12/07 |
Stereocontrolled Aldol Reactions II |
G&A 5.2; O'L 12-15 |
|
| 20 | 12/12 |
Stereocontrolled Aldol Reactions III |
G&A 5.2; O'L 12-15 |
