Reformatsky Reaction& Recent Advancements

1. 1 1 Reformatsky Reaction & Recent Advancements Presented by Naresh Kashyap Deptt. of Medicinal Chemistry 3 rd Semester

2. 2 2 Flow of Presentation Introduction Mechanism & Reaction Conditions Exceptions Advancements Applications Conclusion

3. 3 3 Introduction Reformatsky Reaction History Di scovered 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 SmI 2 ( Kagan reagent) Indium Aluminium with Bismuth(III)chloride Cobalt Solvents THF DMF Et 2 O CH 2 Cl 2 Temperature -78 to 0 o C to rt 5 5

6. 6 Types Intermolecular Intramolecular

7. 7 Comparision with Aldol Reaction Reformatsky Reaction Neutral condition Reformatsky enolate : L ess reactive than lithium enolates or Grignard reagents No n ucleophilic 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. Cp 2 ZrCl 2 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. 19 92 , 114 , 8464-8472

18. 18 18 Conclusion New C-C bond Formation β -hydroxy ester generation from haloesters Lactones formation Linear lengthening of Carbon chain Neutral reaction condition

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