Michel Addition

Michel Addition & recent advancement

1. JAYANTA SAHA MSc Asymmetric Michael Additions: Advancements in Organocatalysis

2. Arthur Michael “ the way how this combination (of malonate ester with unsaturated acid ester) resulted was clearly known by Mr. Claisen and correctly described. Mr. Michael contributed to make the reaction remarkably practical by the use of sodium compounds of malonate and acetoacetate esters and to have substantially generalized .”- Ernst Von Meyer

3. Mechanism Of Micheal addition: Michael, A. J.Prakt.Chem . 1887 , 35 , 349 ; “On the Addition of Sodioacetoacetic and Sodiomalonic Ester to Unsaturated Acid Esters,”

4. 1,2 - Addition 1,4 - Addition R = H, alkyl

5. Classical Reaction Challenges Scope of Nucleophiles (formation of C–C, N, O, S, P Bonds) Alkene Substitution Patterns Scope of Electrophile Control Stereochemistry Catalytically

6. Outline Enamine/Iminium Catalysts Michael Cascades Reductive Michael Hetero-Michael

7. Enamine / Iminium Catalysis MacMillan, D. et.al. J. Am. Chem. Soc. 2005 , 127 , 15051-15053

8. I Imidazolidinone Catalyst MacMillan, D. and Austin, J. J. Am. Chem. Soc. 2002 , 124 , 1172-1173

9. Aromatic Nucleophiles MacMillan, D. et.al. J. Am. Chem. Soc. 2005 , 127 , 15051-15053 .

10. Catalytic Cycle Iminium ( Im ) Enamine ( En ) MacMillan, D. et.al. J. Am. Chem. Soc. 2005 , 127 , 15051-15053 .

11. Mukaiyama - Michael Reaction MacMillan, D. et.al. J. Am. Chem. Soc. 2003 , 125 , 1192-1194 .

12. Chem. Soc. Rev., 2014, 43 , 7430 Aza-Michael reaction

13. Catalytic Cycle Chem. Soc. Rev., 2014, 43, 7430

14. Asymmetric Aza-Michaels Chem. Soc. Rev., 2014, 43, 7430

15. Catalytic Cycle Chem. Soc. Rev., 2014, 43, 7430

16. Outline Enamine/Iminium Catalysts Michael Cascades Reductive Michael Hetero-Michael

17. Michael-Aldol Cascade Jorgensen, K. et.al. Angew . Chem. Int. Ed. 2004 , 43, 1272-1277

18. Michael Cascades Jorgensen, K. et.al. Angew . Chem. Int. Ed. 2004 , 43, 1272-1277

19. Chiral Cyclopentanes Wang, W. et.al. Angew . Chem. Int. Ed. 2007 , 46 , 3732-3734 .

20. Triple Cascade Enders, D. et.al. Nature 2006 , 441 , 861-863

21. Outline Enamine/Iminium Catalysts Michael Cascades Reductive Michael Hetero-Michael

22. Reductive Michael Additions MacMillan, D. et.al. J. Am. Chem. Soc. 2004 , 127 , 32-33

23. Reductive Michael Cyclization List, B. et.al. J. Am. Chem. Soc . 2005 , 127 , 15036-15037

24. Reductive Michael Cascade List, B. et.al. J. Am. Chem. Soc . 2005 , 127 , 15036-15037.

25. Cyclic Reduction MacMillan, D. et.al. J. Am. Chem. Soc. 2006 , 128 , 12662-12663.

26. Outline Enamine/Iminium Catalysts Michael Cascades Reductive Michael Hetero-Michael

27. Asymmetric Hetero-Michael Sulfa-Michael Jørgensen , K. et.al. J. Am. Chem. Soc. 2005 , 127 , 15710-15711 .

28. Tetrahydrothiophenes Jørgensen , K. et.al. J. Am. Chem. Soc . 2006 , 128 , 14986-14991 .

29. Oxa -Michael Cordova, A. et.al. Chem. Eur. J. 2007 , 13 , 574-581; Nicolaou , K.C. et.al. J. Am. Chem. Soc. 2000 , 122 , 9968 .

30. Oxa -Michael RSC Adv. , 2015, 5 , 88133, L .-Y. Cui,ab Y.-H. Wang,ab S.-R. Chen,ab Y.-M. Wangab and Z.-H. Zhou

31. Proposed transition state RSC Adv. , 2015, 5 , 88133, L.-Y. Cui,ab Y.-H. Wang,ab S.-R. Chen,ab Y.-M. Wangab and Z.-H. Zhou