COURSE CONTENT:
PROTECTIVE GROUPS IN ORGANIC SYNTHESIS: The role of protective groups in organic synthesis, Protection for the hydroxyl group, Protection for the carbonyl group, Protection for the cargohyl group, Protection for the thiol group, Protection for the amino group, Deprotection methods.
STEREOCHEMISTRY OF ORGANIC MOLECULES: Stereoisomers, Symmetry, Configuration, Properties and discrimination of stereoisomers, Heterotopic ligands and faces (Prostereoisomerism, Prochirality), Chirality of molecules devoid of chiral centers, Chiroptical properties.
LEARNING OUTCOMES:
After completion of this course, the successful student will be able to:
- specify and to explain the ways, reagents and conditions for protection and deprotection of different functional groups
- write mechanisms of protecting groups introduction and removal reactions
- define and to give examples of orthogonal sets of protecting groups
- use protective groups in the synthesis of organic molecules
- define the stereochemical relationships between structures and determine which molecule is chiral, based on the symmetry arguments
- determine the absolute configuration of the molecule at the stereogenic center and in those without stereogenic center (axial, planar and helical chirality)
- describe methods for experimental determination of the absolute and relative configuration and explain the principles of chiroptical methods
- determine topicity relationships of atoms and groups within the molecule.
|
- 1. T. W. Green, P. G. M. Wuts: Protective Groups in Organic Synthesis, John Wiley&Sons, Inc., New York, 1999.
2. P. J. Kocienski, Protecting Groups, Thieme, Stuttgart, 2005.
3. E. L. Eliel, S. H. Willen, Stereochemistry of Organic Compounds, John Wiley&Sons, Inc., New York, 1999.
- 1. T. W. Green, P. G. M. Wuts: Protective Groups in Organic Synthesis, John Wiley&Sons, Inc., New York, 1999.
2. M. B. Smith, March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, John Wiley & Sons, Inc., New Jersy, 2013.
3. F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry: Part A: Structure and Mechanisms, Springer Science & Business Media, New York, 2000.
4. Eric V. Anslyn, Dennis A. Dougherty, Modern Physical Organic Chemistry, University Science Books, 2006.
5. IUPAC, Commision on Nomenclature of Organic Chemistry, Commision on Physical Organic Chemistry, Basic Terminology of Stereochemistry (Recommendations 1996), Pure & Appl. Chem. 1996, 68, 2193.
|
Pristupačnost
