NPTEL : NOC:Essentials of Oxidation, Reduction and C_C Bond Formation. Application in Organic Synthesis (Chemistry and Biochemistry)

Co-ordinators : Prof. Yashwant D Vankar


Lecture 1 - Introduction to organic synthesis-Importance of selectivity, stereochemistry and Mechanism

Lecture 2 - Sulfur based oxidations of alcohols

Lecture 3 - Sulfur based oxidations and Pummerer rearrangement

Lecture 4 - Further aspects of sulfur and selenium based oxidations

Lecture 5 - Organoselenium chemistry and SeO2 based oxidations

Lecture 6 - SeO2 based oxidation of ketones and Sulfoxide- Sulfenate rearrangement (Mislow-Evans rearrangement)

Lecture 7 - Mechanistic and stereochemical aspects of Mislow-Evans rearrangement and synthetic applications

Lecture 8 - Further synthetic applications of Mislow-Evans rearrangement and Saegusa-Ito oxidation

Lecture 9 - 1,2-Ketone transpositions, Shapiro reaction and Dauben-Michno rearrangement (a case of 1,3-enone transposition)

Lecture 10 - Dess-Martin periodinane oxidation

Lecture 11 - Iodoxybenzoic acid (IBX) based oxidations

Lecture 12 - Silver based oxidations: Prevost reaction and use of Fetizon’s reagent

Lecture 13 - Further aspects of oxidations using Fetizon’s reagent: Mechanism and Stereochemistry

Lecture 14 - Ruthenium tetroxide (and RuCl3/NaIO4) mediated oxidations

Lecture 15 - Tetra-n-propylammonium perruthenate (TPAP) based oxidations, and Tamao-Fleming oxidation

Lecture 16 - Further synthetic and mechanistic aspects of Tamao-Fleming oxidations

Lecture 17 - Oxidations with dimethyl dioxirane (DMDO)

Lecture 18 - Mechanistic aspects of DMDO based oxidations and oxaziridine mediated alpha-hydroxylations of ketones

Lecture 19 - Asymmetric alpha-hydroxylations using oxaziridine based reactions

Lecture 20 - Barton and related reactions (oxidation at unfunctionalised carbons) and synthetic applications

Lecture 21 - beta-Cleavage in Barton and related reactions and miscellaneous oxidations such as TEMPO based oxidations, Pinnick oxidation and pseudomonas putida mediated oxidations

Lecture 22 - Reductions in organic chemistry: Metal hydride (NaBH4 and LiAlH4) mediated reduction

Lecture 23 - Reductions using diisobutylaluminum hydride (DIBAL-H)

Lecture 24 - Further aspects of DIBAL-H based reductions and comparison with mixed chloride hydrides

Lecture 25 - Reductions with Red-Al, and Luche Reductions

Lecture 26 - Further aspects of Luche reduction, stereochemistry in reductions and reduction with LiBH4

Lecture 27 - Reductions with Zn(BH4)2, LiBHEt3 (superhydride) and L and K-selectrides

Lecture 28 - Reductions with LS/KS selectrides and NaCNBH3

Lecture 29 - Dissolving metal reductions (Na, K, Mg) and McMurry coupling using Ti(0)

Lecture 30 - Stereochemistry and mechanistic aspects of McMurry coupling and metal mediated reductions of alpha, beta-unsaturated ketones

Lecture 31 - Silanes [R3SiH, including polymethylhydrosiloxanes (PMHS)] as reducing agents

Lecture 32 - Further aspects of silanes as reducing agents and Barton-McCombie deoxygenation

Lecture 33 - Tributyltinhydride (n-Bu3SnH) based radical based reductions and C-C bond formations

Lecture 34 - Asymmetric synthesis: An introduction

Lecture 35 - Sharpless asymmetric epoxidation: Mechanism, stereochemistry and kinetic resolution

Lecture 36 - Synthetic utility of chiral 2,3-epoxy alcohols obtained from Sharpless epoxidation

Lecture 37 - Katsuki-Jacobsen epoxidation: Mechanism and stereochemistry

Lecture 38 - Further aspects of Katsuki-Jacobsen epoxidation, and Introduction to Sharpless Asymmetric Dihydroxylation

Lecture 39 - Mechanism, stereochemical aspects and synthetic applications of Sharpless Asymmetric Dihydroxylation

Lecture 40 - Asymmetric hydrogenations and reductions using rhodium and ruthenium derived chiral catalysts

Lecture 41 - Asymmetric reduction with oxazaborilidines

Lecture 42 - C-C bond formations: Introduction to enolate, enamine and enol silyl ether based chemistry

Lecture 43 - C-C bond formations using enol silyl ether and imine based chemistry including SAMP and RAMP based asymmetric alkylations

Lecture 44 - Asymmetric C-C bond formations using Oppolzer’s camphorsultams and introduction to directed Aldol reactions

Lecture 45 - Further aspects of Aldol chemistry including the use of boron and silicon enolates

Lecture 46 - C-C bond formations using Evans’ oxazolidinone based chemistry

Lecture 47 - Ireland-Claisen rearrangement: Emphasis of enolate geometry on the stereochemical outcome, and Claisen rearrangements

Lecture 48 - Aromatic Claisen rearrangement, Johnson-Claisen rearrangement and Eschenmoser-Claisen rearrangement and synthetic

Lecture 49 - Bellus-Claisen rearrangement, Aza-Claisen rearrangement, Thia-Claisen rearrangement, Chen-Mapp rearrangement and their synthetic applications

Lecture 50 - Zwitterionic-Claisen rearrangement, Overmann rearrangement, Bamford- Stevens and Shapiro reactions and synthetic applications

Lecture 51 - Introduction to allyl metal additions for C-C bond formation

Lecture 52 - Allylindium chemistry: Mechanism, stereochemistry and synthetic applications

Lecture 53 - Allyltin chemistry: Mechanism, stereochemistry and synthetic applications

Lecture 54 - Chemistry of allylsilanes: Mechanism, stereochemistry and synthetic applications - Part 1

Lecture 55 - Further synthetic aspects of the chemistry of allylsilanes - Part 2

Lecture 56 - Further synthetic aspects of the chemistry of allylsilanes - Part 3

Lecture 57 - Chemistry of Vinylsilanes: Mechanism, Stereochemistry and Synthetic Applications

Lecture 58 - Peterson olefination and further synthetic aspects of vinylsilane chemistry

Lecture 59 - Simmons Smith cyclopropanation: Mechanism, stereochemistry and synthetic applications

Lecture 60 - Course Summary and Conclusion