Asymmetric synthesis and retrosynthesis

Summary

The first part of the course presents the classical methods of asymmetric synthesis. The second part of the course introduces retrosynthesis strategies based on the disconnection approach.

Content

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Learning Prerequisites

Required courses

This course relies on the knowledges and competences gained from: "Fonctions et réactions organiques I - II" and "Chimie Générale avancée II" or equivalent courses.

Important concepts to start the course

In-depth understanding of the polarity and reactivity of the main functional groups (alkenes, carbonyls)

Learning Outcomes

By the end of the course, the student must be able to:

• Apply stereochemistry concepts to the rationalization of stereoselectivity in of reactions in organic chemistry
• Assess / Evaluate which one of several possible transition states is the most favorable for a reaction
• Propose a detailed mechanism for the following reactions: synthesis, reduction and oxidation of alkenes, addition of nucleophiles onto carbonyl compounds, generation and functionalization of enolates, aldol addition, reactions of imines and enamines, conjugate addition
• Analyze stereoselectivity in the following reactions: synthe of imines and enamines, conjugate addition
• Propose a disconnection strategy for multifunctional organic molecules
• Plan a sequence of reactions starting from a retrosynthetic plan
• Compare synthetic routes from efficiency and feasibility standpoints
• Defend a synthetic route based on previous reports in the scientific literature
• Identify disconnections sites in a complex molecule

Teaching methods

Ex cathedra with exercise sessions

Assessment methods

Written exam

Resources

Bibliography

For Part I (Asymmetric Synthesis):

The contents of the course will be displayed using Power Points slides as well as drawings at the blackboard/tablet. Such learning material will be made available for the students on the Moodle website. A script script detailing the contents of the course will be also accessible for download on the Moodle website. Most of the examples in the script will be shown and discussed during the lectures.

For Part II (Rétrosynthèse):

The contents of the course will be detailed on tablet during the lectures. Additional documents and publications will be made available on the Moodle website.

 

Ressources en bibliothèque

• Classics in total synthesis II : More Targets, Strategies, Methods
• Organic Synthesis : The Disconnection Approach

Notes/Handbook

Recommended text books:

Classics in total synthesis II / More Targets, Strategies, Methods
K. C. Nicolaou and S. A. Snyder
Ed: Wiley-VCH

Organic Synthesis, The Disconnection Approach
Stuart Warren
Ed: John Wiley & Sons

The Logic of Chemical Synthesis
E.J. Corey and X.-M. Cheng
Ed: John Wiley & Sons

 

Websites

• http://library.epfl.ch/beast?isbn=0471509795
• http://library.epfl.ch/beast?isbn=3527306846
• http://library.epfl.ch/beast?isbn=9780470712368

Moodle Link

• https://go.epfl.ch/CH-335

Prerequisite for

Total Synthesis of Natural Products