Special synthesis techniques in organic chemistry

A.Y. 2018/2019
6
Max ECTS
48
Overall hours
SSD
CHIM/06
Language
Italian
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
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.
Course syllabus and organization

Single session

Responsible
Lesson period
First semester
Course syllabus
Course objective
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.

Course content
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.

Recommended reading
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).

Prerequisites
Basic knowledge of organic chemistry, reactivity of functional groups, stereochemistry.

Assessment methods
Written (possibility for a partial examination (3 cfu) during the course) and oral examination (optional)

Language of instruction
Italian

Other information
Attendance: recommended
Type of course: traditional
CHIM/06 - ORGANIC CHEMISTRY - University credits: 6
Lessons: 48 hours
Professor: Silvani Alessandra
Professor(s)