Construction and transformation of organic molecules 1200-1KTMCHOWL
Tools for construction and transformation of molecules:
The formation of carbon-hydrogen bonds: additions to the C = C bonds, addition to the C = O bonds, s stereochemically controlled homogeneous hydrogenation, enantioselective hydrosilylation.
Additions to the C = N bonds, hydrogenation and asymmetric hydrogen transfer of imines, imines hydrosilylation, 1,4-dihydropyridine as reducting agents for imines, oxime ethers, and related compounds.
The formation of carbon-oxygen bonds: the formal addition of an oxygen atom to alkene molecule, Katsuki-Sharpless epoxidation, Jacobsen epoxidation, Julia-Colonna epoxidation of activated alkenes, stereoselective dihydroxylation.
The formation of carbon-nitrogen bonds: stereoselective and tosyloaziridination and aziridination of alkenes.
Additions to olefinic bond: Stereocontrolled addition of HY-type reagents, nucleophilic addition of heteroatoms to olefins, α-functionalization of carbonyl compounds.
The formation of carbon-carbon bonds: alkylation of chiral enolates controlled by activating group, catalytic alkylation of enolates. Stereocontrolled aldol reactions, organokatalysis using amino acid derivatives, ureas, and thioureas. Nucleophilic addition to the carbonyl groups: by carbon sp3, sp2, and sp nucleophiles allyl; propargylation and alkenylation of carbonyl groups, additions of stabilized carbanions, stereoselective cyanosilylation.
Additions to the C = N bonds: Mannich and Strecker reactions, addition of carbon sp3, sp2, and sp nucleophiles.
Coupling reactions catalyzed with π-allyl complexes of transition metals.
Catalytic activation of C-H bonds.
Sigmatropic rearrangements: stereocontrolled Claisen rearrangement, Cope and ene reactions. Enantioselective Stetter reaction. Baylis-Hillman reaction and related processes.
Aromatic electrophilic and nucleophilic substitution. The replacement of hydrogen or other groups in aromatic systems.
The cyclization processes: cycloaddition reactions; Diels-Alder reactions, and hetero-Diels-Alder reactions and their stereochemical control. Enantioselective [3 + 2] cycloaddition, Simmons-Smith cyclopropanation. Complex pseudocyclization processes, multicomponent reactions.
Carbo- and heterocyclization processes: intramolecular Michael addition, Robinson annulation, hydroboration reaction, Pauson-Khand reaction.
Cyclization catalyzed by rhodium complexes. Enantioselective Heck reaction, the Nazarov reaction, Pictet-Spengler cyclization - stereochemical aspects. Enantioselective metathesis processes.
Type of course
Mode
Prerequisites (description)
Course coordinators
Learning outcomes
Deepening of the knowledge of modern methods of construction and transformation of organic molecules with particular emphasis on the stereochemical aspects is expected.
Assessment criteria
Written exam.
Practical placement
Not expected.
Bibliography
1. John McMurry, Chemia Organiczna, PWN Warszawa 2000, tom 1 i 2
2. Jacek Skarżewski, Wprowadzenie do Syntezy Organicznej, PWN Warszawa, Łódź 1999
3. Robert T. Morrison, Robert N. Boyd, Chemia Organiczna, PWN Warszawa 1997
4. Jacek Gawroński, Krystyna Gawrońska, Stereochemia w Syntezie Organicznej, PWN
Warszawa 1988
5. Przemysław Mastalerz, Chemia Organiczna, PWN Warszawa 1984
6. Robert M. Silverstein, Francis X. Webster, David J. Kiemle, Spektroskopowe metody
identyfikacji związków organicznych, PWN Warszawa 2007
7. Richard C. Larock, Comprehensive Organic Transformations, Wiley VCH, 1999
8. Michael B. Smith, Jerry March, March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Wiley-Interscience, 2007
Additional information
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