CY7340 : MODERN CONCEPTS IN ORGANIC SYNTHESIS

Additions to C-X bonds

Organometallic reagents of Al, Cu, Ti, Zr, C, Zn, Cd, Hg and Ce metals. Nucelophilic addition to imines, imine derivatives and carboxylic acid derivates; Carbanions stabilized by N,B, S, Si and Se, containing groups; epoxidation and skeletal reorganization; allyl organometallics, transition metal enolates, homoeneolates, metalloenamines, enol ethers, asymmetric synthesis with enol ethers; Eschenmoser coupling reactions; Passserini and Ugi reaction.

Carbon-carbon o-bond formation

Alkylation of enols,enolates; stabilized and non-stabilized carbanions; cyclization reactions; coupling reactions and rearrangements. Additions to and substitutiion at C-C ? bonds Organocuprates and conjugate reactins; nucleophiles with cationic pentadienyl- metal complexes; kroganopalladium reagents; carbometallation.

Combining C-C ? bonds

Ene reactions; oxa-di-?-metals photoisomerisation, transition metal mediated cycloadditions; retrogade Diels-Alder reactions; Nazarov cationic cylization; charge-transfer accelerated cyclization.

Heteroatom manipulations

Synthesis of glycosides, sulphides, sulphoxides, phosphonium ylides and related compounds, Ritter type eaction; protecting groups; Nef reaction; reductive elimination; vicinal deoxygenation and vicinal desilylation.

Oxidation

Oxidation by remote functionalisation, microbial methods; epoxidation and asymmetric epoxidation; glycol formation; electrochemical oxidation; oxidative rearrangements; solid-support oxidants and electron transfer reactions.

Reduction

Reduction by metal hydrides; asymmetric hydrogenation; enzymatic reduction; hydro-zirconation, – boration, – aluminatin and – silylation reaction.

Miscellaneous

Transition metals in organic synthesis; Birch-Pearson, Dotz, Heck-Stille, Hegedus, Mcmurray, Noyori, Pauson-Khand, Sharpless, Tebbe-Grubbs and Vollhardt reactions; asymmetric synthesis; chiral auxiliaries; catalytic enantioselective reactions; chemzymes. Antibody catalysis; biological-chemical transformations. Structural elucidation and reaction dynamics by multi-dimensional NMR spectroscopy and crystal diffraction methods; novel separation methods.

References:

1. Much emphasis will be made on reports in current literature pertaining to Organic Synthesis. The following references can be followed for general guidelines.
2. B.M. Trost (ed.) Comprehensive Organic Synthesis: Selectivity, Strategy and Efficiency in Modern Organic Chemistry, Pergamon Press, Oxford, Vols 1-9, 1991.
3. E.J. Corey and X..-M.Cheng, The Logic of Chemical Synthesis, Wiley, New York, 1989.
4. J.D. Morrison (Series Ed.) Asymmetric Synthesis Academic Press, New York.
5. J.P. Collman, L.S. Hegedus, J.R. Norton and R.G. Finke, Principles and Applications of Organotransition Metal Chemistry. University Science Books, Mill Valley, California, 1987.
6. Dieter Seebach, “Organic Synthesis – Where Now?”, Angew. Chem.Int.Ed.Engl.29, (1990) 1320.