Universidade Nova de Lisboa

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Faculdade de Ciências e Tecnologia

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

50

Teaching language

Português

Objectives


This is a continuation of the course in asymmetric organic chemistry intiated in QOA1 but with an emphasis on mechanistic aspects. It is hoped to fuse material from physical chemistry and general organic chemistry to form a firm foundation in the area of chemical kinetics and thermodynamics with a strong emphasis on asymmetric chemistry from the second cycle bioorganic course. Recognising the strong interdisciplinary nature of this course it is hoped to include material from the areas of computational chemistry and structural analysis. 

Subject matter


Mechanisms in Asymmetric Chemistry: General principles of kinetics and thermodynamics. Application to asymmetric systems. The importance of knowledge about the conformational profile of the reagents. Procjiral centres. Relative enrgies of transition states in asymmetric reactions: enantiomeric and diastereomeric transition states. Use of chiral auxiliaries, chiral catalysts. The principles of resolution, kinetic resolution and dynamic kinetic resolution.

Free Radical Chemistry: Basic concepts of free radical reactions. Detection and characterisation of free radicals. Free radicals localised on carbon and heteroatoms. Radical anions and radical cations. Classification and mechanisms in free radical reactions. Methods for the generation of free radicals. Radical/radical reactions. Stereoselective radical reactions. Substitution and addition. Cyclisations and rearrangments. Electron transfer reactions and oxidation. Functionalisation of C-H bonds and functional group conversions. Synthetic and industrial applications.

Bibliography

English

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.



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