CHM609A - Principles Of Organic Chemistry
Prerequisites: Only for Ph.D. Students
3-0-0-9
Course Contents
Stereochemistry:
Conformation of acyclic and cyclic molecules, Geometrical and Optical Isomerism. Dynamic stereochemistry: Conformation and reactivity.
Reactions:
Mechanistic and Stereochemical aspects of: Baeyer-Villiger, Claisen (including Johnson and Ireland modifications), Wittig rearrangements. Ene and metalloene reactions, Barton reaction.
Reactive Intermediates:
An overview and revision of the chemistry of carbenes, nitrenes, radicals, carbocations (including non-classical carbocation), carbanions (homoenolate anion) and benzynes with emphasis on stereochemical implications wherever applicable.
Oxidation:
Swern, Dess-Martin, Prevost, dimethyl dioxirane, transition metal catalyzed oxidations, oxidations at unfunctionalized carbons, asymmetric Sharpless epoxidation and dihydroxylation, Jacobsen’s epoxidation: Mechanism, stereochemistry and applications in organic synthesis.
Reduction:
Reduction of carbonyl compounds and C-C multiple bonds: Using Al and B based reagents (e.g. DIBAL, Red-Al, NaBH4-CeCl3.7H2O etc.), low valent Ti species, microbial reductions (NADH models), Qxazaborolidine, BINAP, BINAL based reductions.
C-C Bond Formation:
[2+2], [3+2] and [4+2] cycloadditions, Enolate chemistry (including silicon chemistry).
Synthetic Applications: Synthesis of some typical natural products.
Photochemistry:
Topics
Current Course Information
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Books and References
March, J., Advanced Organic Chemistry, 4th ed, 1999.
Nasipuri, D., Stereochemistry of Organic Compounds, 2nd ed, 1995.
Carey and Sundberg, Advanced Organic Chemistry, Part I and II, 4th ed., 2000.
Clayden, Greeves, Warren, and Wothers, Organic Chemistry, 1st ed, 2001