Reformatsky Reaction& Recent Advancements
- 1. 1 1 Reformatsky Reaction & Recent Advancements Presented by Naresh Kashyap Deptt. of Medicinal Chemistry 3rd Semester
- 2. 2 2 Flow of Presentation Introduction Mechanism & Reaction Conditions Exceptions Advancements Applications Conclusion
- 3. 3 3 Introduction Reformatsky Reaction History Discovered by Russian Chemist, Sergey Nikolaevich Reformatsky in 1887 Ber. Dtsch. Chem. Ges. 1887, 20 ,1210-1211 Pure Appl. Chem. 2008, 80, 891-901
- 4. 4 4 Mechanism Tetrahedron 2004, 60, 9325-9374
- 5. Reaction Conditions Metals Zinc Chromium SmI2 (Kagan reagent) Indium Aluminium with Bismuth(III)chloride Cobalt Solvents THF DMF Et2O CH2Cl2 Temperature -78 to 0oC to rt 5 5
- 6. 6 Types Intermolecular Intramolecular
- 7. 7 Comparision with Aldol Reaction Reformatsky Reaction Neutral condition Reformatsky enolate: Less reactive than lithium enolates or Grignard reagents No nucleophilic addition to the ester group Aldol Reaction Alkaline or acidic condition
- 8. 8 8 Exceptions O-alkylation Instead of C-alkylation Tetrahedron 2004, 60, 9325-9374
- 9. 9 9 Advancements One pot Reformatsky Reaction Pure Appl. Chem. 2008, 80, 891-901
- 10. 10 10 Chiral Auxiliary Introduced Reformatsky Reaction Synthesis of Neooxazolomycin Tetrahedron 2004, 60, 9325-9374
- 11. Cp2ZrCl2 Induced Reformatsky Reaction 11 11 Appl. Organometal. Chem. 2011, 25, 470-475
- 12. Electrochemically Supported Reformatsky Reaction 12 12 Tetrahedron 2004, 60, 9325-9374
- 13. 13 Reformatsky Reaction in Absence of Solvent 13 J. Org. Chem. 1991, 56, 4333-4334
- 14. 14 14 Applications Synthesis of Indane acetic acid Pure Appl. Chem. 2008, 80, 891-901
- 15. 15 Total Synthesis of Acutiphycin J. Am. Chem. Soc. 2006, 128, 15106-15107
- 16. 16 Intramolecular Reformatsky Reaction in Total Synthesis of B-ring System of Taxol Chem. Eur. J. 1999, 5, 121-161
- 17. 17 Total Synthesis of (+) 10,10-difluorothromboxane J. Am. Chem. Soc. 1992, 114, 8464-8472
- 18. 18 18 Conclusion New C-C bond Formation 硫-hydroxy ester generation from haloesters Lactones formation Linear lengthening of Carbon chain Neutral reaction condition
- 19. 19 19