Asymmetric Organic Chemistry II
Code
7209
Academic unit
Faculdade de Ciências e Tecnologia
Department
Departamento de Química
Credits
6.0
Teacher in charge
Maria Manuela Marques Araújo Pereira
Weekly hours
3
Teaching language
Português
Objectives
The teaching program on asymmetric organic chemistry, which began in QOA I, will be continued but with an emphasis on the mechanistic aspects. Material from physical chemistry and gneral organic chemistry courses will be combined to create a wider base in kinetics and thermodynamics with emphasis on asymmetric chemistry for the Bioorganc chemistry Masters course. The interdisciplinarity of this course will be strengthened by interlinking other courses such as computational chemistry and structural analysis.
The following themes will be taught but within a flexible framework and can be adjusted depending upon the profile of the students attending the masters course in Bioorganic chemistry.
Subject matter
Asymmetric induction
Foundation
1,2- and 1,3-stereoinduction
Long distance stereoinduction
Orienting groups and chelation effects
Stereoelectronic effects (hindrance and electrostatic repulsion
Strategies based upon chiral reagent, chiral catalyst or chiral substrate.
The ‘Chiral pool’ Asymmetric synthesis using asymmetric natural products as starting material.
Chiral auxiliaries. Chiral catalysts (asymmetric hydrogenation, asymmetric epoxidation and dihydroxylation).
Diastereoselectividade in aldol and related reactions.
Aymmetric organocatalysis: nucleophilic substitution in aliphatic compounds, nucleophilic addition to double bonds, carbonyls and imines, cycloaddition reactions, Oxidation and reduction.
Biotransformations and the use of enzymes in organic synthesis.
Asymmetric catalysis: Comparison of metal based and organocatalytic systems.
Enantioselective radical processes.
Strategy in natural product synthesis.
Bibliography
1. Mechanism and Theory in Organic Chemistry, 3rd edition, H.Lowry and K.S. Richardson, Harper e Row Publishers, 1987.
2. Investigation of Organic Reactions and their Mechanisms, Maskill, Blackwell, 2006.
3. Free Radical Chain Reactions in Organic Synthesis, W. B. Motherwell, D. Crich, Ac. Press (1991).
4. Stereoselectivity in Synthesis, Tse-Lok Ho, John Wiley-Interscience, 1999.
5. Catalysis in Asymmetric Synthesis, J. M. J. Williams. Blackwell, 1999.
Teaching method
Theoretical lectures are given in way to avoid monotony. During the lectures experimental results are used to demonstrate concepts which exemplify the importance of the understanding of chemistry. Problems sessions are an essential part of the course and at least four hours per week are dedicated to this. Although in the first sessions the lecturer leads the students into discussions it is expected that later the students will be encouraged take over this initiative.
When justified molecular models are used as a visual aid. 3D graphics and other audio-visual aids are used whenever possible.
Problem sessions are also very important for the lecturer to identify difficulties that the students may have in their understanding and to find solutions to these difficulties by discussion. This is done in such a way that the high level of the course is maintained
Students have access to a web page created on the moodle platform where they will find online support documents for the theoretical and TP classes.