Asymmetric Organic Chemistry II

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.

General characterization

Code

7209

Credits

6.0

Responsible teacher

Maria Manuela Marques Araújo Pereira

Hours

Weekly - 3

Total - Available soon

Teaching language

Português

Prerequisites

Available soon

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.

Evaluation method

-Analysis of a paper
   The paper has several transformations.

   Each student makes the presentation (10 min) - preparing a compound from the previous one (20% of the evaluation). It involves presentation of the mechanism involved.

-Solving a weekly problem. Individual work. Email by the morning of class. Resolution will be made in class (15min) and / or published in CLIP. (20% of the evaluation)
 
-Examination about the paper.  (2 examinations - 45 minutes) (30% of the evaluation)
 
-Final examination . (30% evaluation)

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.

Programs

Programs where the course is taught: