Prerequisite: Basic concepts of stereochemistry, naming absolute configuration, prochirality, enantiotopic and diastereotopic faces.
Introduction, stereospecific and regiospecific synthesis – Cram’s rule, chiral auxiliary, asymmetric induction, principles & examples of asymmetric synthesis (Michael addition, Diel’s-Alder reaction, epoxidation, reductions and hydroboration).
Concept of dynamic enantiomerism. Role of enzymes in chiral synthesis.
Oxidation of hydrocarbons, alcohol, carbonyl compound, amines, thiol, Reduction of hydrocarbon carbonyl ,epoxides and nitroso acid &its derivative, nitrocompound ,oximes azo compound ,disulphide sulphonyl chloride.
Application of following reagents with specific examples.
Organoboron reagents (IBBN, CATB, IpC2BH, PINB). Organosilicon compounds, Triflates. Trimethylsilyl iodide, baker’s yeast. Hypervalent iodine, Phase transfer catalysts, Lithium dimethycuprate, Lithium disopropylamide (LDA), dicyclohexyl carbodiimide(DCC) 1,3-dithiane, DDQ, Heck, Vilsmayer, Mukaiyama and McMurray reaction and Suzuki and Sonogashira coupling.
Homogenous catalysis ;elementary steps in homogeneous catalysis,ligand exchange ;dissociation and coordination ,oxidative addion reductive elimination insertion de –insertion and beta –elimination
Steric effect; ligand size flexibility and symmetry asymmetric homogeneous homocatalysis catalysis (homogenous catalysis without metals )catalyst recovery and recycling ,organocatalysis.)
Heteronenous analysis ; prepration of solid catalyst ,catalyst stability.catalytic convertor,surface organometalic chemistry .liquid-liquid catalytic system ,aqueous biphasic catalysis .biphasic catalyst using ionic liquid ,phase transfer catalyst (miscelles, Surfactants,)green catalysts (zeolite, silica, alumina, clay, polymer, cyclodextrin, etc,), chiral pool as a source of enantio selective catalyst and auxiliaries.
Basic principles of green chemistry, application of non-conventional techniques in organic synthesis and natural products (ultrasonic, microwave and electrosynthesis). Solid state synthesis and synthesis under solvent free conditions. Use of ionic solvents, biocatalysts, nanoparticles etc.
Drug Discovery and Development
A rational approach to drug design and drug development of following drugs: cimetidine, oxamniquine.
1. Advance organic chemistry ;reaction mechanism and structure ,fourth edition jerry march ; john wiley and sons asia pvt ltd, New Delhi 2007.
2 Green chemistry ;introductory text M.Lancaster royal society of chemistry (London).
3 Catalysis ; concepts and green application gadi rithenberg wiley –VCH,2008.
4 Principle of asymmetric synthesis ,R,E gawley ,J.aube.pergmon oxford 1996,vol 14
5 Selectivity in organic synthesis ,Robert,s,ward,john wiley 1999.
Links:
[1] https://chemistry.iisuniv.ac.in/courses/subjects/advanced-course-organic-chemistry-5
[2] https://chemistry.iisuniv.ac.in/academic-year/2014-2015