Asymmetric Organic Chemistry II
Code
7209
Academic unit
Faculdade de Ciências e Tecnologia
Department
Departamento de Química
Credits
6.0
Teacher in charge
Maria Teresa Barros Silva
Weekly hours
3
Total hours
64
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.
Selective 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
The theoretical part will be integrated with the theoretical and practical component. The communication will be performed by existing audio-visual techniques making use of slides. Also will use the chalkboard to a proximity communication and a greater interaction with students. A proactive approach is always required.
The theoretical-practical classes will be coordinated with the lectures and it is intended that there is discussion among all the stakeholders.