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CATALYTIC METHODS IN ORGANIC SYNTHESIS

Antonio MASSA CATALYTIC METHODS IN ORGANIC SYNTHESIS

0522300041
DEPARTMENT OF CHEMISTRY AND BIOLOGY "ADOLFO ZAMBELLI"
EQF7
CHEMISTRY
2020/2021

OBBLIGATORIO
YEAR OF COURSE 1
YEAR OF DIDACTIC SYSTEM 2016
PRIMO SEMESTRE
CFUHOURSACTIVITY
540LESSONS
112EXERCISES
ANTONIO MASSA T Curriculum
Objectives
THE COURSE AIMS TO PROVIDE INFORMATION AND METHODS FOR THE RESOLUTION OF COMPLEX PROBLEMS OF CURRENT ORGANIC SYNTHESIS. PARTICULAR EMPHASIS WILL BE DEVOTED TO THE APPLICATIONS OF CATALYSTS OF VARIOUS NATURE IN THE SYNTHESIS AND TRANSFORMATIONS OF ORGANIC COMPOUNDS, IN THE STUDY OF MECHANISMS OF THE MAIN TRANSFORMATIONS, THE PROPERTIES OF CHIRAL MOLECULES AND ENANTIOSELECTIVE CATALYTIC METHODS.

THE MAIN KNOWLEDGE ACQUIRED BY THE STUDENTS WILL REGARD TO:

- RELATIONSHIP BETWEEN MOLECULAR STRUCTURE AND EXPERIMENTAL REACTIVITY OF MONO- AND POLY-FUNCTIONAL MOLECULES.
- APPLICATIONS OF METAL CATALYSIS IN THE MAIN TRANSFORMATIONS AND ENANTIOSELECTIVE VERSIONS OF THESE REACTIONS.
- RECENT DEVELOPMENTS OF ORGANOCATALYSIS IN ASYMMETRIC SYNTHESIS.
- MECHANISTIC FEATURES OF MAIN REACTIONS.
- METHODOLOGICAL STRATEGIES FOR THE SYNTHESIS OF PHARMACOLOGICALLY ACTIVE CHIRAL PRODUCTS.

THE MAIN SKILLS DEVELOPED BY THE STUDENTS WILL BE:

- SOLVING PROBLEMS RELATED TO THE SYNTHESIS AND TRANSFORMATION OF COMPLEX MOLECULES.
- CRITICAL ANALYSIS OF EXPERIMENTAL DATA AND OF THE STEREOCHEMICAL ASPECT OF A REACTION.
- APPLICATION OF REACTIONS PROMOTED BY CATALYSTS TO SUBSTRATES OF DIFFERENT NATURE.
- INSTRUMENTAL ANALYSIS FOR THE DETERMINATION OF THE PURITY OF STEREOISOMERIC MIXTURES OF ORGANIC COMPOUNDS
Prerequisites
BASIC ORGANIC CHEMISTRY AT A BACHELOR DEGREE LEVEL
Contents
- INTRODUCTION TO THE COURSE.
- CATALYSIS AND ASYMMETRIC SYNTHESIS. KINETIC RESOLUTION. MAYR ELECTROPHILICITY AND NUCLEOFILITY SCALES FOR THE PREDICTION OF THE REACTIVITY. DIFFERENT ORGANOCATALYTIC ACTIVATION MODES OF CARBONYL COMPOUNDS.
- ALKYLATION OF CARBONYL COMPOUNDS. ALDOL, MANNICH AND MICHAEL REACTIONS. ENANTIOSELECTIVE VERSIONS.
- USE OF TRANSITION METAL CATALYSTS IN CARBON-CARBON AND CARBON-HETEROATOM BOND FORMING REACTIONS; ACTIVATION OF CARBON-HYDROGEN BONDS; PALLADIUM CATALYZED REACTIONS (SUZUKI REACTIONS, HECK, SONOGASHIRA VARIANTS); HARTWIG-BUCHWALD REACTIONS.
- OXIDATION REACTIONS. ASYMMETRIC SHARPLESS EPOSSIDATION OF ALLYLIC ALCOHOLS. JACOBSEN ASYMMETRIC EPOSSIDATION OF ALKENES. ASYMMETRIC ORGANOCATALYTIC EPOXIDATION BY DIOXIRANES. OPENING AND REARRANGEMENT REACTIONS OF EPOXIDES UNDER BASIC AND ACIDIC CONDITIONS.
- REDUCTION REACTIONS. ASYMMETRIC HYDROGENATION REACTIONS. ORGANOCATALYTIC APPROACH TO REDUCTIONS.
- ONE-POT, CASCADE AND MULTICOMPONENT REACTIONS FOR THE SYNTHESIS OF STRUCTURALLY COMPLEX MOLECULES.
Teaching Methods
THE COURSE CONTEMPLATES LECTURES WITH SUPPORT OF ELECTRONIC PRESENTATIONS AND THE SOLVING OF RELEVANT PROBLEMS ON THE BLACKBOARD. ALL TEACHING MATERIALS WILL BE MADE AVAILABLE TO STUDENTS AT THE END OF EACH LESSON AS FILES IN PDF FORMAT.
MOREOVER, EXERCISES WILL BE PROVIDED ON THE APPLICATIONS OF THE MECHANISMS OF THE MAIN REACTIONS STUDIED IN THE COURSE.
Verification of learning
THE EXAM OCCURS EXCLUSIVELY THROUGH AN ORAL INTERVIEW ON THE
THEORETICAL AND METHODOLOGICAL CONTENTS AS
INDICATED IN THE COURSE PROGRAM. THE AIM IS TO ESTABLISH THE LEVEL OF
KNOWLEDGE AND CAPACITY OF
UNDERSTANDING REACHED BY THE STUDENT, AND TO VERIFY THE ABILITY OF
THE PRESENTATION USING THE
APPROPRIATE TERMINOLOGY.
Texts
- F. A. CAREY AND R. J. SUNDBERG: "ADVANCED ORGANIC CHEMISTRY" FIFTH EDITION, PART B. SPRINGER.

- HANDBOOK OF GREEN CHEMISTRY, EDITED BY P. T. ANASTAS, "GREEN CATALYSIS" VOL. 1
More Information
FOR FURTHER INFORMATION: AMASSA@UNISA.IT
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