Special synthesis techniques in organic chemistry

A.Y. 2020/2021
Overall hours
Learning objectives
The course intends to explain the basic concepts in the synthesis of complex organic molecules. The most significant methodologies of the modern organic synthesis will be discussed, also including asymmetric ones, with attention to both the general aspects and illustrative applications. Also some special techniques will be described, among the most recent and of wide spread, which are aimed to improve the efficiency, the economy and the environmental impact of the chemical organic synthesis.
Expected learning outcomes
The course allows a consolidation of the knowledge on the general strategies of formation of the single and multiple carbon-carbon bond; provides basic skills of asymmetric synthesis; allows a first contact with special techniques applied to chemical synthesis. The student acquires the ability to solve the synthesis of molecules with different degrees of structural complexity.
Course syllabus and organization

Single session

Lesson period
First semester
The lessons will be held on the Microsoft Teams platform and can be followed both synchronously on the basis of the first semester timetable and asynchronously, because will be registered and left available to students on the same platform.
The exam will take place using the Microsoft Teams platform or, where regulations allow, in the presence (see Evaluation method).
If the regulations concerning social distancing will allow it, additional face-to-face exercise activities will be held periodically.
Any updates related to the evolution of the legislation imposed by Covid-19 will be published on time in the Ariel page of the course.
Course syllabus
Basic concepts in the modern synthesis of complex organic molecules: in-depth study on alkylation of enolates, aldol reaction, acylation at carbon, conjugate addition of enolates; controlling the geometry of double bonds; elements of stereochemistry, diastereoselectivity (2 cfu).
Synthesis of optically active molecules: kinetic resolution, chiral pool methodology, chiral auxiliaries, asymmetric catalysis; asymmetric catalysis in organic synthesis: metal catalysis, enzymatic catalysis, organocatalysis (1 cfu).
Transition metal complexes in organic synthesis: the basic chemistry of organopalladium complexes; Heck, Sonogashira, Suzuki, Negishi, Stille reactions; olefin metathesis (1 cfu).
Special techniques: microwave, ultrasounds, ionic liquids in organic synthesis; not conventional solvents, polymer supported reagents; solid phase synthesis; combinatorial chemistry; flow chemistry (2 cfu).
Within the course, also guided exercises will be proposed to students, aimed to a better understanding of the contents and to a full application in practical examples.
Prerequisites for admission
Basic knowledge of organic chemistry, reactivity of functional groups, stereochemistry.
Prerequisites: Organic Chemistry 1 and 2
Teaching methods
Attendance: recommended
Type of course: traditional
Language of instruction: Italian
Web page (available on the Ariel web site - teaching online Unimi).
Teaching Resources
Didactic material from the teacher (available on the Ariel web site - teaching online Unimi).
For consultation: Advanced Organic Chemistry. Part A, Structures and Mechanisms. Part B, Reaction and Synthesis. Francis A. Carey, Richard J. Sundberg, Springer New York Inc. (recommended for students inclined to Advanced Organic Chemistry curricula).
Assessment methods and Criteria
Written exam, with open questions and application exercises (possibility for a partial written exam during the course). On request, the assessment can be completed with an oral exam.
CHIM/06 - ORGANIC CHEMISTRY - University credits: 6
Lessons: 48 hours
Professor: Silvani Alessandra