Alessandra LATTANZI | ADVANCED SYNTHETIC METHODS IN ORGANIC CHEMISTRY

cod. CB22300001

ADVANCED SYNTHETIC METHODS IN ORGANIC CHEMISTRY

	CB22300001
	DEPARTMENT OF CHEMISTRY AND BIOLOGY "ADOLFO ZAMBELLI"
	EQF7
	CHEMISTRY
	2025/2026

CURRICULUM BIOMOLECULAR CHEMISTRY

	OBBLIGATORIO
	YEAR OF COURSE 1
	YEAR OF DIDACTIC SYSTEM 2025
	AUTUMN SEMESTER

TEACHING UNITS

SSD	CFU	HOURS	ACTIVITY	TYPE OF ACTIVITY
CHIM/06	7	56	LESSONS	COMPULSORY SUBJECTS, CHARACTERISTIC OF THE CLASS
CHIM/06	2	24	EXERCISES	COMPULSORY SUBJECTS, CHARACTERISTIC OF THE CLASS
CHIM/06	3	36	LAB	COMPULSORY SUBJECTS, CHARACTERISTIC OF THE CLASS

PROFESSORS

	ALESSANDRA LATTANZI T Curriculum
	GIORGIO DELLA SALA Curriculum
	SARA MENINNO Curriculum

	Objectives
	GENERAL OBJECTIVE: DURING THE COURSE A DEEPER KNOWLEDGE ON THE CLASSICAL AND MOST RECENT METHODS FOR THE REGION- AND STEREOSELECTIVE FORMATION OF CARBON-CARBON AND CARBON-HETEROATOM BOND FORMATION WILL BE PROVIDED TO THE STUDENT. KNOWLEDGE AND UNDERSTANDING ABILITY. THE STUDENT WILL ACQUIRE KNOWLEDGE CONCERNING: -FUNCTIONALIZATION REACTIONS OF ORGANIC COMPOUNDS; -STEREOCONTROL FEATURES IN THE REACTION STUDIED -SYNTHESIS OF COMPLEX ORGANIC MOLECULES MEDIATED BY DIFFERENT CLASSES OF CATALYSTS AND REACTION CONDITIONS - REACTION MECHANISM ABILITY TO COMPREHEND AND APPLY KNOWLEDGE. THE STUDENT WILL BE ABLE TO -CRITICALLY DISCUSS THE REACTION MECHANISM -RESOLVE PROBLEMS RELATED TO THE SYNTHESIS OF ORGANIC MOLECULES OF DIFFERENT COMPLEXITY AUTONOMY OF JUDGEMENT. THE STUDENT WILL BE ABLE TO -DEVELOP CRITICAL ABILITY TO CHOOSE THE MOST EFFICIENT SYNTHETIC STRATEGY TO ACCESS ORGANIC COMPOUNDS -EVALUATE AND CHOOSE THE REAGENTS AND REACTION CONDITIONS MOST SUITABLE FOR THE SYNTHETIC STRATEGY USING THE ON-LINE TOOLS (SCIFINDER); -COMPARE THE DATA OBTAINED WITH THOSE REPORTED IN THE SCIENTIFIC LITERATURE AND PROVIDE SOLUTION FOR OPTIMIZATION OF THE PROCESSES COMUNICATION ABILITY. THE STUDENT WILL BE ABLE TO: -DESCRIBE IN A CORRECT WAY THE REACTION, INCLUDING THE FORMATION OF INTERMEDIATES AND THE MECHANISM -COMMUNICATE THE ACQUIRED KNOWLEDGE IN WRITTEN AND ORAL FORMS, USING A TECHNICAL-SCIENTIFIC LANGUAGE LEARNING ABILITY. THE STUDENT WILL BE ABLE TO: - EXPAND AND UPDATE THE KNOWLEDGE RELATED TO ORGANIC CHEMISTRY, USINGADVANCED TEXTBOOKS AND RESEARCH ARTICLE FORM THE SCIENTIFIC LITERATURE AND CHEMICAL DATA BANKS -BEING ABLE TO UNDERSTAND THE DATA AND SYNTHETIC PROTOCOLS REPORTED IN SCIENTIFIC PUBLICATIONS FOR THE SYNTHESIS OF ORGANIC MOLECULES

GENERAL OBJECTIVE: DURING THE COURSE A DEEPER KNOWLEDGE ON THE CLASSICAL AND MOST RECENT METHODS FOR THE REGION- AND STEREOSELECTIVE FORMATION OF CARBON-CARBON AND CARBON-HETEROATOM BOND FORMATION WILL BE PROVIDED TO THE STUDENT.
KNOWLEDGE AND UNDERSTANDING ABILITY. THE STUDENT WILL ACQUIRE KNOWLEDGE CONCERNING:
-FUNCTIONALIZATION REACTIONS OF ORGANIC COMPOUNDS;
-STEREOCONTROL FEATURES IN THE REACTION STUDIED
-SYNTHESIS OF COMPLEX ORGANIC MOLECULES MEDIATED BY DIFFERENT CLASSES OF CATALYSTS AND REACTION CONDITIONS
- REACTION MECHANISM
ABILITY TO COMPREHEND AND APPLY KNOWLEDGE. THE STUDENT WILL BE ABLE TO
-CRITICALLY DISCUSS THE REACTION MECHANISM
-RESOLVE PROBLEMS RELATED TO THE SYNTHESIS OF ORGANIC MOLECULES OF DIFFERENT COMPLEXITY
AUTONOMY OF JUDGEMENT. THE STUDENT WILL BE ABLE TO
-DEVELOP CRITICAL ABILITY TO CHOOSE THE MOST EFFICIENT SYNTHETIC STRATEGY TO ACCESS ORGANIC COMPOUNDS
-EVALUATE AND CHOOSE THE REAGENTS AND REACTION CONDITIONS MOST SUITABLE FOR THE SYNTHETIC STRATEGY USING THE ON-LINE TOOLS (SCIFINDER);
-COMPARE THE DATA OBTAINED WITH THOSE REPORTED IN THE SCIENTIFIC LITERATURE AND PROVIDE SOLUTION FOR OPTIMIZATION OF THE PROCESSES
COMUNICATION ABILITY. THE STUDENT WILL BE ABLE TO:
-DESCRIBE IN A CORRECT WAY THE REACTION, INCLUDING THE FORMATION OF INTERMEDIATES AND THE MECHANISM
-COMMUNICATE THE ACQUIRED KNOWLEDGE IN WRITTEN AND ORAL FORMS, USING A TECHNICAL-SCIENTIFIC LANGUAGE
LEARNING ABILITY. THE STUDENT WILL BE ABLE TO:
- EXPAND AND UPDATE THE KNOWLEDGE RELATED TO ORGANIC CHEMISTRY, USINGADVANCED TEXTBOOKS AND RESEARCH ARTICLE FORM THE SCIENTIFIC LITERATURE AND CHEMICAL DATA BANKS
-BEING ABLE TO UNDERSTAND THE DATA AND SYNTHETIC PROTOCOLS REPORTED IN SCIENTIFIC PUBLICATIONS FOR THE SYNTHESIS OF ORGANIC MOLECULES

	Prerequisites
	BASIC KNOWLEDGE PREVIOUSLY AQUIRED BY THE STUDENT IN THE COURSES OF ORGANIC CHEMISTRY I AND II

	Contents
	THE COURSE IS DIVIDED INTO THREE MODULES: IN MODULE A, THE TEACHING LESSONS ARE ABOUT THE FOLLOWING TOPICS: STEREOSELECTIVE ALPHA AND BETA ALKYLATION OF CARBONYL COMPOUNDS (12 H) AND THEIR ALPHA,BETA-UNSATURATED COUNTERPARTS (3 H). ASYMMETRIC METHODS OF ALPHA AND BETA HETEROFUNCTIONALIZATION OF CARBONYL COMPOUNDS AND THEIR ALPHA,BETA-UNSATURATED COUNTERPARTS (4 H). ALDOL REACTION AND ASYMMETRIC VERSIONS, INCLUDING ORGANOCATALYTIC SYSTEMS (6 H). SULFUR YLIDES AND THEIR APPLICATIONS (1 H). WITTIG OLEFINATION VARIANTS, PETERSON OLEFINATION (4 H). MAGNESIUM, LITIUM AND COPPER-ORGANOMETALLIC COMPOUNDS AND THEIR APPLICATIONS (7 H). STEREOSELECTIVE OXIDATION OF ALKENES (7 H). RING-OPENING AND REARRANGEMENTS OF EPOXIDES (2 H). FUNDAMENTAL REACTIONS OF ALLYLIC AND VINYLIC ORGANOSILICON COMPOUNDS (3 H). ASYMMETRIC METAL CATALYSED HYDROGENATIONS OF OLEFINS AND METAL-FREE REDUCTIONS (4 H). ONE-POT, CASCADE AND MULTICOMPONENT REACTIONS AND SELECTIVE EXAMPLES ON THEIR APPLICATIONS FOR THE SYNTHESIS OF HETEROCYCLIC COMPOUNDS (3 H). IN MODULE B, RETROSYNTHETIC EXCERCISES WILL BE PRESENTED ON THE REACTIONS DISCUSSED IN MODULE A. IN MODULE C, PRACTICAL SYNTETIC APPLICATIONS OF THE REACTIONS STUDIED IN MODULE A TO PREPARE DIFFERENT COMPOUNDS WILL BE PERFORMED IN THE LABORATORY. THE COMPOUNDS WILL BE ISOLATED AND STRUCTURALLY CHARACTERIZED. AROUND 60% OF MODULE A IS DEVOTED TO CARBON-CARBON AND CARBON-HETEROATOM BOND FORMATION, 20% TO OXIDATION PROCESSES AND 20% TO REDUCTION AND CASCADE PROCESSES.

Contents

THE COURSE IS DIVIDED INTO THREE MODULES:
IN MODULE A, THE TEACHING LESSONS ARE ABOUT THE FOLLOWING TOPICS: STEREOSELECTIVE ALPHA AND BETA ALKYLATION OF CARBONYL COMPOUNDS (12 H) AND THEIR ALPHA,BETA-UNSATURATED COUNTERPARTS (3 H). ASYMMETRIC METHODS OF ALPHA AND BETA HETEROFUNCTIONALIZATION OF CARBONYL COMPOUNDS AND THEIR ALPHA,BETA-UNSATURATED COUNTERPARTS (4 H). ALDOL REACTION AND ASYMMETRIC VERSIONS, INCLUDING ORGANOCATALYTIC SYSTEMS (6 H). SULFUR YLIDES AND THEIR APPLICATIONS (1 H). WITTIG OLEFINATION VARIANTS, PETERSON OLEFINATION (4 H). MAGNESIUM, LITIUM AND COPPER-ORGANOMETALLIC COMPOUNDS AND THEIR APPLICATIONS (7 H). STEREOSELECTIVE OXIDATION OF ALKENES (7 H). RING-OPENING AND REARRANGEMENTS OF EPOXIDES (2 H). FUNDAMENTAL REACTIONS OF ALLYLIC AND VINYLIC ORGANOSILICON COMPOUNDS (3 H). ASYMMETRIC METAL CATALYSED HYDROGENATIONS OF OLEFINS AND METAL-FREE REDUCTIONS (4 H). ONE-POT, CASCADE AND MULTICOMPONENT REACTIONS AND SELECTIVE EXAMPLES ON THEIR APPLICATIONS FOR THE SYNTHESIS OF HETEROCYCLIC COMPOUNDS (3 H).
IN MODULE B, RETROSYNTHETIC EXCERCISES WILL BE PRESENTED ON THE REACTIONS DISCUSSED IN MODULE A.
IN MODULE C, PRACTICAL SYNTETIC APPLICATIONS OF THE REACTIONS STUDIED IN MODULE A TO PREPARE DIFFERENT COMPOUNDS WILL BE PERFORMED IN THE LABORATORY. THE COMPOUNDS WILL BE ISOLATED AND STRUCTURALLY CHARACTERIZED.
AROUND 60% OF MODULE A IS DEVOTED TO CARBON-CARBON AND CARBON-HETEROATOM BOND FORMATION, 20% TO OXIDATION PROCESSES AND 20% TO REDUCTION AND CASCADE PROCESSES.

	Teaching Methods
	MODULES A AND B COMPRISE TEACHING LESSONS (80 H) AND EXERCISES AT THE BLACKBOARD IN THE CLASSROOM ON THE ORGANIC TRANSFORMATIONS DISCUSSED IN MODULE A. THE ATTENDANCE OF BOTH MODULES IS HIGHLY RECOMENDED. MODULE C (36 H) IS LABORATORY PRACTISE CONCERNING THE SYNTHESIS AND CHARACTERIZATION OF SELECTED COMPOUNDS. THE FINAL DATA OF THE LABORATORY WORK HAVE TO BE WRITTEN IN REPORTS TO DELIVER TO THE TUTOR BEFORE THE FINAL ORAL EXAMINATION. 75% ATTENDANCE OF MODULE C IS COMPULSORY AND IT WILL BE ASSURED BY THE LABORATORY TUTOR.

Teaching Methods

MODULES A AND B COMPRISE TEACHING LESSONS (80 H) AND EXERCISES AT THE BLACKBOARD IN THE CLASSROOM ON THE ORGANIC TRANSFORMATIONS DISCUSSED IN MODULE A. THE ATTENDANCE OF BOTH MODULES IS HIGHLY RECOMENDED. MODULE C (36 H) IS LABORATORY PRACTISE CONCERNING THE SYNTHESIS AND CHARACTERIZATION OF SELECTED COMPOUNDS. THE FINAL DATA OF THE LABORATORY WORK HAVE TO BE WRITTEN IN REPORTS TO DELIVER TO THE TUTOR BEFORE THE FINAL ORAL EXAMINATION. 75% ATTENDANCE OF MODULE C IS COMPULSORY AND IT WILL BE ASSURED BY THE LABORATORY TUTOR.

	Verification of learning
	THE AIM OF THE FINAL EXAM IS TO CHECK THAT THE LEARNING OUTCOMES HAVE BEEN ACHIEVED. FORMATIVE ASSESSMENT IS CERTIFIED BY AN ORAL EXAMINATION OF AROUND 45 MINUTES, WITH A FINAL MARK EXPRESSED BETWEEN 18 AND 30, COMPRISING QUESTIONS AND DISCUSSION ABOUT THE CONTENT OF THE TEACHING COURSE AND THE LABORATORY WORK. THE ABILITY TO COMMUNICATE THE TOPICS AND TO PROPOSE A SYNTHETIC SEQUENCE OF A TARGET MOLECULE PROPOSED BY THE TEACHING EXAMINER, WILL BE ALSO ASSESSED DURING THE ORAL EXAMINATION. THE FULL MARK AND HONORS IS ACHIEVABLE WHEN THE STUDENT DEMONSTRATES HIGH ABILITY TO SOLVE UNCOMMON PROBLEMS (OR NOT TREATED DURING THE LESSONS) PROPOSED DURING THE ORAL EXAM.

Verification of learning

THE AIM OF THE FINAL EXAM IS TO CHECK THAT THE LEARNING OUTCOMES HAVE BEEN ACHIEVED. FORMATIVE ASSESSMENT IS CERTIFIED BY AN ORAL EXAMINATION OF AROUND 45 MINUTES, WITH A FINAL MARK EXPRESSED BETWEEN 18 AND 30, COMPRISING QUESTIONS AND DISCUSSION ABOUT THE CONTENT OF THE TEACHING COURSE AND THE LABORATORY WORK. THE ABILITY TO COMMUNICATE THE TOPICS AND TO PROPOSE A SYNTHETIC SEQUENCE OF A TARGET MOLECULE PROPOSED BY THE TEACHING EXAMINER, WILL BE ALSO ASSESSED DURING THE ORAL EXAMINATION. THE FULL MARK AND HONORS IS ACHIEVABLE WHEN THE STUDENT DEMONSTRATES HIGH ABILITY TO SOLVE UNCOMMON PROBLEMS (OR NOT TREATED DURING THE LESSONS) PROPOSED DURING THE ORAL EXAM.

	Texts
	F. A. CAREY AND R. J. SUNDBERG, ADVANCED ORGANIC CHEMISTRY B AND A, (FIFTH EDITION) SPRINGER, 2007. J. MARCH, ADVANCED ORGANIC CHEMISTRY, J. WILEY & SONS; NEW YORK (IV ED.) TEACHING MATERIAL ABOUT MORE RECENT DEVELOPMENTS FROM THE SCIENTIFIC LITERATURE WILL BE AVAILABLE FROM THE TUTOR.

	More Information
	FOR FURTHER INFORMATION SEND AN E-MAIL TO: LATTANZI@UNISA.IT WEBPAGE: https://docenti.unisa.it/003250/en/curriculum

Lessons Timetable

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Alessandra LATTANZI | ADVANCED SYNTHETIC METHODS IN ORGANIC CHEMISTRY