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Course10410112764 lectures

Essentials of Oxidation, Reduction and C-C Bond Formation. Application in Organic Synthesis

Prof. Yashwant D Vankar · IIT Bombay

Start with lecture 1 At NPTEL

Lectures

Week 1

  1. Lecture 1 : Introduction to organic synthesis-Importance of selectivity, stereochemistry and Mechanism Video
  2. Lecture 2 : Sulfur based oxidations of alcohols Video
  3. Lecture 3 : Sulfur based oxidations and Pummerer rearrangement Video
  4. Lecture 4 : Further aspects of sulfur and selenium based oxidations Video
  5. Lecture 5 : Organoselenium chemistry and SeO2 based oxidations Video

Week 2

  1. Lecture 6 : SeO2 based oxidation of ketones and Sulfoxide- Sulfenate rearrangement (Mislow-Evans rearrangement) Video
  2. Lecture 7 : Mechanistic and stereochemical aspects of Mislow-Evans rearrangement and synthetic applications Video
  3. Lecture 8 : Further synthetic applications of Mislow-Evans rearrangement and Saegusa-Ito oxidation Video
  4. Lecture 9 : 1,2-Ketone transpositions, Shapiro reaction and Dauben-Michno rearrangement (a case of 1,3-enone transposition) Video
  5. Lecture 10 : Dess-Martin periodinane oxidation Video

Week 3

  1. Lecture 11 : Iodoxybenzoic acid (IBX) based oxidations Video
  2. Lecture 12 : Silver based oxidations: Prevost reaction and use of Fetizon's reagent Video
  3. Lecture 13 : Further aspects of oxidations using Fetizon's reagent: Mechanism and Stereochemistry Video
  4. Lecture 14 : Ruthenium tetroxide (and RuCl3/NaIO4) mediated oxidations Video
  5. Lecture 15 : Tetra-n-propylammonium perruthenate (TPAP) based oxidations, and Tamao-Fleming oxidation Video

Week 4

  1. Lecture 16 : Further synthetic and mechanistic aspects of Tamao-Fleming oxidations Video
  2. Lecture 17 : Oxidations with dimethyl dioxirane (DMDO) Video
  3. Lecture 18 : Mechanistic aspects of DMDO based oxidations and oxaziridine mediated alpha-hydroxylations of ketones Video
  4. Lecture 19 : Asymmetric alpha-hydroxylations using oxaziridine based reactions Video
  5. Lecture 20 : Barton and related reactions (oxidation at unfunctionalised carbons) and synthetic applications Video

Week 5

  1. Lecture 21 : beta-Cleavage in Barton and related reactions and miscellaneous oxidations such as TEMPO based oxidations, Pinnick oxidation and pseudomonas putida mediated oxidations Video
  2. Lecture 22 : Reductions in organic chemistry: Metal hydride (NaBH4 & LiAlH4) mediated reduction Video
  3. Lecture 23 : Reductions using diisobutylaluminum hydride (DIBAL-H) Video
  4. Lecture 24 : Further aspects of DIBAL-H based reductions and comparison with mixed chloride hydrides Video
  5. Lecture 25 : Reductions with Red-Al, and Luche Reductions Video

Week 6

  1. Lecture 26 : Further aspects of Luche reduction, stereochemistry in reductions & reduction with LiBH4 Video
  2. Lecture 27 : Reductions with Zn(BH4)2, LiBHEt3 (superhydride) & L & K-selectrides Video
  3. Lecture 28 : Reductions with LS/KS selectrides and NaCNBH3 Video
  4. Lecture 29 : Dissolving metal reductions (Na, K, Mg) & McMurry coupling using Ti(0) Video
  5. Lecture 30 : Stereochemistry and mechanistic aspects of McMurry coupling & metal mediated reductions of alpha, beta-unsaturated ketones Video

Week 7

  1. Lecture 31 : Silanes [R3SiH, including polymethylhydrosiloxanes (PMHS)] as reducing agents Video
  2. Lecture 32 : Further aspects of silanes as reducing agents & Barton-McCombie deoxygenation Video
  3. Lecture 33 : Tributyltinhydride (n-Bu3SnH) based radical based reductions & C-C bond formations Video
  4. Lecture 34 : Asymmetric synthesis: An introduction Video
  5. Lecture 35 : Sharpless asymmetric epoxidation: Mechanism, stereochemistry and kinetic resolution Video

Week 8

  1. Lecture 36 : Synthetic utility of chiral 2,3-epoxy alcohols obtained from Sharpless epoxidation Video
  2. Lecture 37 : Katsuki-Jacobsen epoxidation: Mechanism and stereochemistry Video
  3. Lecture 38 : Further aspects of Katsuki-Jacobsen epoxidation, & Introduction to Sharpless Asymmetric Dihydroxylation Video
  4. Lecture 39 : Mechanism, stereochemical aspects and synthetic applications of Sharpless Asymmetric Dihydroxylation Video
  5. Lecture 40 : Asymmetric hydrogenations and reductions using rhodium and ruthenium derived chiral catalysts Video

Week 9

  1. Lecture 41 : Asymmetric reduction with oxazaborilidines Video
  2. Lecture 42 : C-C bond formations: Introduction to enolate, enamine and enol silyl ether based chemistry Video
  3. Lecture 43 : C-C bond formations using enol silyl ether and imine based chemistry including SAMP and RAMP based asymmetric alkylations Video
  4. Lecture 44 : Asymmetric C-C bond formations using Oppolzer's camphorsultams and introduction to directed Aldol reactions Video
  5. Lecture 45 : Further aspects of Aldol chemistry including the use of boron and silicon enolates Video

Week 10

  1. Lecture 46 : C-C bond formations using Evans' oxazolidinone based chemistry Video
  2. Lecture 47 : Ireland-Claisen rearrangement: Emphasis of enolate geometry on the stereochemical outcome, and Claisen rearrangements Video
  3. Lecture 48 : Aromatic Claisen rearrangement, Johnson-Claisen rearrangement and Eschenmoser-Claisen rearrangement and synthetic Video
  4. Lecture 49 : Bellus-Claisen rearrangement, Aza-Claisen rearrangement, Thia-Claisen rearrangement, Chen-Mapp rearrangement and their synthetic applications Video
  5. Lecture 50 : Zwitterionic-Claisen rearrangement, Overmann rearrangement, Bamford- Stevens and Shapiro reactions and synthetic applications Video

Week 11

  1. Lecture 51 : Introduction to allyl metal additions for C-C bond formation Video
  2. Lecture 52 : Allylindium chemistry: Mechanism, stereochemistry and synthetic applications Video
  3. Lecture 53 : Allyltin chemistry: Mechanism, stereochemistry and synthetic applications Video
  4. Lecture 54 : Chemistry of allylsilanes: Mechanism, stereochemistry and synthetic applications (Part 1) Video
  5. Lecture 55 : Further synthetic aspects of the chemistry of allylsilanes (Part 2) Video

Week 12

  1. Lecture 56 : Further synthetic aspects of the chemistry of allylsilanes (Part 3) Video
  2. Lecture 57 : Chemistry of vinylsilanes: Mechanism, stereochemistry and synthetic applications Video
  3. Lecture 58 : Peterson olefination and further synthetic aspects of vinylsilane chemistry Video
  4. Lecture 59 : Simmons-Smith cyclopropanation: Mechanism, stereochemistry and synthetic applications Video
  5. Lecture 60 : Course Summary and conclusion Video

Live Session

  1. Live Session 15-02-2022 Video
  2. Live Session 04-05-2022 Video
  3. Live Session 27-02-2024 Video
  4. Live Session 24-02-2025 Video

Syllabus and materials

At NPTEL, as the course publishes them.

Credits and licence

Institution
IIT Bombay
Department
Chemistry and Biochemistry
Teacher
Prof. Yashwant D Vankar
Level
Undergraduate
Language
English
Subjects
Chemistry
Source
NPTEL
Licence
CC BY-NC-SA, as NPTEL states it. Non-commercial use only. NPTEL's terms
Attribution
NPTEL states: "Distributed under Creative Commons Attribution-ShareAlike / CC BY - NC - SA", beside a BY-NC-SA badge.
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