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Reformatsky Reaction& Recent Advancements

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NARESH KASHYAP

The document summarizes the Reformatsky reaction, an important carbon-carbon bond forming reaction discovered in 1887. It describes the reaction mechanism and conditions, such as the use of zinc, chromium, or indium as reagents and solvents like THF, DMF, or Et2O. The document outlines exceptions to the reaction, recent advancements like one-pot or chiral auxiliary introduced versions, and applications to the synthesis of various compounds, concluding that the Reformatsky reaction allows new C-C bond formation and 硫-hydroxy ester or lactone generation under neutral conditions.

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1 1 Reformatsky Reaction & Recent Advancements Presented by Naresh Kashyap Deptt. of Medicinal Chemistry 3rd Semester
2 2 Flow of Presentation Introduction Mechanism & Reaction Conditions Exceptions Advancements Applications Conclusion
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 Mechanism Tetrahedron 2004, 60, 9325-9374
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 Types Intermolecular Intramolecular
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 Exceptions O-alkylation Instead of C-alkylation Tetrahedron 2004, 60, 9325-9374
9 9 Advancements One pot Reformatsky Reaction Pure Appl. Chem. 2008, 80, 891-901
10 10 Chiral Auxiliary Introduced Reformatsky Reaction Synthesis of Neooxazolomycin Tetrahedron 2004, 60, 9325-9374
Cp2ZrCl2 Induced Reformatsky Reaction 11 11 Appl. Organometal. Chem. 2011, 25, 470-475
Electrochemically Supported Reformatsky Reaction 12 12 Tetrahedron 2004, 60, 9325-9374
13 Reformatsky Reaction in Absence of Solvent 13 J. Org. Chem. 1991, 56, 4333-4334
14 14 Applications Synthesis of Indane acetic acid Pure Appl. Chem. 2008, 80, 891-901
15 Total Synthesis of Acutiphycin J. Am. Chem. Soc. 2006, 128, 15106-15107
16 Intramolecular Reformatsky Reaction in Total Synthesis of B-ring System of Taxol Chem. Eur. J. 1999, 5, 121-161
17 Total Synthesis of (+) 10,10-difluorothromboxane J. Am. Chem. Soc. 1992, 114, 8464-8472
18 18 Conclusion New C-C bond Formation 硫-hydroxy ester generation from haloesters Lactones formation Linear lengthening of Carbon chain Neutral reaction condition
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Reformatsky Reaction& Recent Advancements