This course provides an advanced knowledge and understanding of stereochemistry of organic compounds, principles of asymmetric synthesis and methods.

Educational Goals:

-to develop a knowledge base of organic stereochemistry and methods for achieving stereoselectivity.

-to master an understanding of reactivity principles associated with stereoselective synthesis.

-to gain the ability to propose stereoselective method for a given chiral product.

-to develop fundamental critical thinking skills and analogous reasoning.

Topics covered:

Brush up History of stereochemistry (chirality, catalysis), Principles of Stereochemistry and Asymmetric Synthesis (Point groups, symmetry classes; Classification of isomers, groups, faces, Local chirality, stereogenicity, chirotopicity, symmetry criteria, systematic notation, axial and planar chirality, stereo-differentiating reactions), Acyclic Conformational Analysis (Alkanes, carbon heteroatom bonds, Alkenes, allylic strain, Orbital analysis of double bonded groups, Atropisomerism), Cyclic Conformational Analysis (Small rings, Cyclohexane, cyclohexene, reactivity of common rings and bicyclic systems, Torsional strain, medium sized rings, Heterocycles), Stereoelectonic Effects (Hyperconjugation, Stereoelectronic effects on reactivity, fragmentation), Lewis base catalysis (Basic principles, historical survey) Organocatalysis (Iminium ion, enamine, endiamine, thiourea H-bond, NHC carbene, chiral counter ion) Hydrogen Bonding Catalysis, Principles of Asymmetric of Catalysis (Diastereomeric interactions and nonlinear effects, Asymmetric amplification and reservoir effects, Autocatalysis and absolute asymmetric synthesis, Asymmetric autoinduction), Kinetic Resolution (Basic principles of kinetic resolution, epoxides alcohols, Kinetic Resolution: SAE, alkenes, Dynamic kinetic resolution, Dynamic kinetic asymmetric transformations, Parallel kinetic resolution, Desymmetrization reactions), Multifunctional Catalysis, Enantioselective Pd, Ni, Mo mediated Allylic Asymmetric Alkylation and C-H functionalization, Asymmetric dearomatizationEnantioselective biomimetic cyclizationChiral Atom Economy, Applications of Asymmetric Catalysis in Total Synthesis