SPRING 2000

This information effective for Spring 2000.
Check with instructor the first day of class for any changes.

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Chemistry

[CHEM-240F-01]

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Chemistry 240F: Selectivity and Strategy in Organic Synthesis

Instructor: Rebecca Braslau
Office: Thimann 337, tel. 459-3087
First 5 Weeks of Spring Quarter 2000
Tuesday, Thursday 10:00- 11:45 Thimann Labs 101
Discussion Section: Monday nights, 7:30 pm Thimann 339 April 10, 17 and 24.

This is a 5 week course designed to follow Chemistry 240E (Modern Synthetic Reactions) offered by Professor Singaram. Prerequisite: 240E or consent of instructor.

Assignments and Exams:

There will be two exams: a midterm worth 100 pts on April 18, and a final exam worth 150 points on April 27. Three sets of homework (15 pts per set) will be assigned during the half quarter, and should be turned into Rebecca's mailbox by 10:00 am on Monday the day of the discussion section. Attendance at the discussion section Monday nights is Mandatory.

Books on 1-Day Reserve:

March, Advanced Organic Chemistry
Noyori, Asymmetric Catalysis in Organic Synthesis
Ager, Asymmetric Synthetic Methodology
Mulzer, Organic Synthetic Highlights
Fuhrhop & Penzlin, Organic Synthesis: Concepts, Methods and Starting Materials
Seyden-Penne, Chiral auxiliaries and ligands in asymmetric synthesis
Morrison, Asymmetric synthesis Vol. 4 (contains a list of optically active starting materials)

The following topics will be covered:

Introduction

Literature and References

Starting Materials

Retrosynthetic Analysis

Selectivity

Selected Reactions and Processes

Cyclizations

Baldwin's Rules

Thorpe-Ingold Effect

Cationic, Anionic, Radical & Organometallic Cyclizations

Other 5-Membered Ring Synthesis

Pauson-Khand

Carbonyl Condensations

Nazarov Cyclization

Palladium TMM

[3 + 2] Dipolar Cycloadditions

Control of Stereochemistry

Relative Diastereoselectivity

Ring Systems

Acyclic Stereocontrol

Felkin-Ahn, Cram Chelation Control

Aldol Stereochemistry

Allylation of Carbonyls

Reconnective Strategy

Absolute Stereochemistry

Relative Diastereoselectivity using Optically Pure Materials

Chirons

Classic Resolution

Chiral Auxiliaries

Enantioselectivity

Stoichiometric Asymmetric Induction

Kinetic Resolution

Catalytic Asymmetric Induction

Asymmetric Amplification

Synthetic Strategy

Convergence

Atom Economy

Strategic Bonds

Biomimetic Strategy

Key Reaction Strategy

Formal Synthesis

Computers