Details of CH3104 (Autumn 2016)
Level: 3 | Type: Theory | Credits: 3.0 |
Course Code | Course Name | Instructor(s) |
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CH3104 | Stereochemistry and asymmetric synthesis | Sureshkumar Devarajulu |
Syllabus |
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Acyclic stereochemistry
Representation of molecules in Fischer, saw horse, flying-wedge and Newman formulae and their inter translations, symmetry elements, molecular chirality. Configuration: stereogenic units i) stereocentres: systems involving 1,2,3 centres, stereogenicity, chirotopicity. seudoasymmetric (D/L and R/ S descriptor, threo/erythro and syn/anti nomenclatures ii) stereoaxis: chiral axis in allenes and biphenyls, R/S descriptor; cis/trans, syn/anti, E/Z descriptors (for C=C, C=N). Optical activity of chiral compounds: specific rotation, optical purity (enantiomeric excess), Topicity of ligands and faces (elementary idea): Pro-R, Pro-S and Re/Si descriptors. Conformation: Conformational nomenclature, eclipsed, staggered, gauche and anti; dihedral angle, torsion angle, energy barrier of rotation, relative stability of conformers on the basis of steric effect, dipole-dipole interaction, H -bonding etc. Cyclic stereochemistry Cyclic Stereochemistry: Baeyer strain theory. Conformational analysis: cyclohexane, mono and disubstituted cyclohexane, symmetry properties and optical activity. Conformation & reactivity in cyclohexane system: elimination (E2), rearrangement, nucleophilic substitution (SN1, SN2, NGP) Asymmetric synthesis Introduction to asymmetric synthesis, Basic principles of a Symmetric synthesis-Definition of stereospecific, stereoselective, enantioselective and diastereoselective reactions Importance of asymmetric synthesis, conditions for an efficient asymmetric synthesis, energetic considerations, strategies for asymmetric synthesis-advantages and limitations of each strategy, analytical methods for determining enantiomeric excess. Resolving agents and resolution of racemic compounds. Asymmetric synthesis on chiral substrate Nucleophilic addition to ?chiral carbonyl compounds; Prediction of stereochemistry, Crams rule and related modifications. Double stereo differentiation; matched pair and mismatched pair; examples from aldol condensation and hydroboration reactions. Asymmetric synthesis using chiral auxiliary Chiral auxiliaries derived from proline, camphor, menthol and other chiral pool sources. SAMP/RAMP hydrazines, and other pyrrolidine derivatives. Asymmetric synthesis using chiral catalysts Asymmetric alkylation and allylation of carbonyl compounds. Asymmetric hydrogenation. Sharpless epoxidation, dihydroxylation, amino-hy droxylation of alkenes. |
References |
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Course Credit Options
Sl. No. | Programme | Semester No | Course Choice |
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1 | IP | 1 | Core |
2 | IP | 3 | Not Allowed |
3 | IP | 5 | Not Allowed |
4 | MR | 1 | Not Allowed |
5 | MR | 3 | Not Allowed |
6 | MS | 5 | Core |
7 | RS | 1 | Not Allowed |
8 | RS | 2 | Not Allowed |