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C-H Insertion Story Justin Du Bois associate professor : University of Stanford B.S. : University of California at Berkeley (1992) Ph.D. : California Institute.

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Presentation on theme: "C-H Insertion Story Justin Du Bois associate professor : University of Stanford B.S. : University of California at Berkeley (1992) Ph.D. : California Institute."— Presentation transcript:

1 C-H Insertion Story Justin Du Bois associate professor : University of Stanford B.S. : University of California at Berkeley (1992) Ph.D. : California Institute of Technology (1997) (Erick M. Carreira) NIH Postdoctoral fellow : Massachusetts Institute of Technology (1997-1999) (Stephen J. Lippard)

2 A Rh-Catalyzed C-H Insertion Reaction for the Oxidative Conversion of Carbamates to Oxazolidinones Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed.. 2001, 40, 598-600.

3 A Rh-Catalyzed C-H Insertion Reaction for the Oxidative Conversion of Carbamates to Oxazolidinones (optimization) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed.. 2001, 40, 598-600. Base : K 2 CO 3, Na 2 HPO 4, 2,6-di-tert- butyl-4-pyridine, BaO, MgO Oxydant : PhI=O, PhI(O2CCF3)2. PhI(OMe)2, 2-iodosobenzoic acid

4 A Rh-Catalyzed C-H Insertion Reaction for the Oxidative Conversion of Carbamates to Oxazolidinones (scope) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed.. 2001, 40, 598-600.

5 A Rh-Catalyzed C-H Insertion Reaction for the Oxidative Conversion of Carbamates to Oxazolidinones (mechanism) Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed.. 2001, 40, 598-600.

6 Synthesis of 1,3-Difunctionalized Amine Derivatives through Selective C-H Bond Oxidation Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936.

7 Synthesis of 1,3-Difunctionalized Amine Derivatives through Selective C-H Bond Oxidation (scope) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936.

8 Synthesis of 1,3-Difunctionalized Amine Derivatives through Selective C-H Bond Oxidation (extension) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936.

9 Stereoselective Organozinc Addition Reactions to 1,2-Dihydropyrans for the Assembly of Complex Pyran Structures Steinhuebel, D. P.; Fleming, J. J.; Du Bois, J. Org. Lett. 2002, 4, 293-295.

10 Enantioselective Synthesis of the Bromopyrrole Alkaloids Manzacidin A and C by Stereospecific C-H Bond Oxidation Wehn, P. M.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950-12951.

11 Enantioselective Synthesis of the Bromopyrrole Alkaloids Manzacidin A and C by Stereospecific C-H Bond Oxidation (retrosynthesis) Wehn, P. M.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950-12951.

12 Enantioselective Synthesis of the Bromopyrrole Alkaloids Manzacidin A and C by Stereospecific C-H Bond Oxidation (hydrogenation) Wehn, P. M.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950-12951.

13 Enantioselective Synthesis of the Bromopyrrole Alkaloids Manzacidin A and C by Stereospecific C-H Bond Oxidation (synthesis) Wehn, P. M.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950-12951.

14 A Unique and Highly Efficient Method for Catalytic Olefin Aziridination Guthikonda, K.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 13672-13673.

15 Novel Iminium Ion Equivalents Prepared through C-H Oxidation for the Stereocontrolled Synthesis of Functionalized Propargylic Amine Derivatives Fleming, J. J.; Fiori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 2028-2029.

16 Novel Iminium Ion Equivalents Prepared through C-H Oxidation for the Stereocontrolled Synthesis of Functionalized Propargylic Amine Derivatives (iminium ion equivalents synthesis) Fleming, J. J.; Fiori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 2028-2029.

17 Novel Iminium Ion Equivalents Prepared through C-H Oxidation for the Stereocontrolled Synthesis of Functionalized Propargylic Amine Derivatives (alkynylzinc addition) Fleming, J. J.; Fiori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 2028-2029.

18 Novel Iminium Ion Equivalents Prepared through C-H Oxidation for the Stereocontrolled Synthesis of Functionalized Propargylic Amine Derivatives (alkynylzinc addition : scope) Fleming, J. J.; Fiori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 2028-2029.

19 Novel Iminium Ion Equivalents Prepared through C-H Oxidation for the Stereocontrolled Synthesis of Functionalized Propargylic Amine Derivatives (extension) Fleming, J. J.; Fiori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 2028-2029.

20 Stereochemical Models for Rh-Catalyzed Amination Reactions of Chiral Sulfamates (scope) Wehn, P. M.; Lee, J.; Du Bois, J. Org. Lett. 2003, 5, 4823-4826.

21 Stereochemical Models for Rh-Catalyzed Amination Reactions of Chiral Sulfamates (rational) Wehn, P. M.; Lee, J.; Du Bois, J. Org. Lett. 2003, 5, 4823-4826.

22 Stereochemical Models for Rh-Catalyzed Amination Reactions of Chiral Sulfamates (rational) Wehn, P. M.; Lee, J.; Du Bois, J. Org. Lett. 2003, 5, 4823-4826.

23 Stereochemical Models for Rh-Catalyzed Amination Reactions of Chiral Sulfamates (rational) Wehn, P. M.; Lee, J.; Du Bois, J. Org. Lett. 2003, 5, 4823-4826.

24 Stereochemical Models for Rh-Catalyzed Amination Reactions of Chiral Sulfamates (aziridination : scope) Wehn, P. M.; Lee, J.; Du Bois, J. Org. Lett. 2003, 5, 4823-4826.

25 Stereochemical Models for Rh-Catalyzed Amination Reactions of Chiral Sulfamates (aziridination : rational) Wehn, P. M.; Lee, J.; Du Bois, J. Org. Lett. 2003, 5, 4823-4826.

26 Expanding the Scope of C-H Amination through Catalyst Design Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378-15379.

27 Expanding the Scope of C-H Amination through Catalyst Design Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378-15379.

28 Expanding the Scope of C-H Amination through Catalyst Design Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378-15379.

29 Expanding the Scope of C-H Amination through Catalyst Design Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378-15379.

30 Deacylative Oxidation Strategy for the Preparation of  -Functionalized Carbonyls Brodsky, B. H.; J. J.; Du Bois, J. Org. Lett. 2004, 6, 2619-2621.

31 Rh-Catalyzed Amination of Ethereal C-H Bonds: AVersatile Strategy for the Synthesis of Complex Amines Fiori, K. W.; Fleming, J. J.; Du Bois, J. Angew. Chem., Int. Ed.. 2004, 43, 4349-4352.

32 Rh-Catalyzed Amination of Ethereal C-H Bonds: AVersatile Strategy for the Synthesis of Complex Amines Fiori, K. W.; Fleming, J. J.; Du Bois, J. Angew. Chem., Int. Ed.. 2004, 43, 4349-4352.

33 Rh-Catalyzed Amination of Ethereal C-H Bonds: AVersatile Strategy for the Synthesis of Complex Amines Fiori, K. W.; Fleming, J. J.; Du Bois, J. Angew. Chem., Int. Ed.. 2004, 43, 4349-4352.

34 Rh-Catalyzed Amination of Ethereal C-H Bonds: AVersatile Strategy for the Synthesis of Complex Amines Fiori, K. W.; Fleming, J. J.; Du Bois, J. Angew. Chem., Int. Ed.. 2004, 43, 4349-4352.

35 Rh-Catalyzed Amination of Ethereal C-H Bonds: AVersatile Strategy for the Synthesis of Complex Amines Fiori, K. W.; Fleming, J. J.; Du Bois, J. Angew. Chem., Int. Ed.. 2004, 43, 4349-4352.

36 Rh-Catalyzed Amination of Ethereal C-H Bonds: AVersatile Strategy for the Synthesis of Complex Amines Fiori, K. W.; Fleming, J. J.; Du Bois, J. Angew. Chem., Int. Ed.. 2004, 43, 4349-4352.

37 Rh-Catalyzed Amination of Ethereal C-H Bonds: AVersatile Strategy for the Synthesis of Complex Amines Fiori, K. W.; Fleming, J. J.; Du Bois, J. Angew. Chem., Int. Ed.. 2004, 43, 4349-4352.

38 Rh-Catalyzed Amination of Ethereal C-H Bonds: AVersatile Strategy for the Synthesis of Complex Amines Fiori, K. W.; Fleming, J. J.; Du Bois, J. Angew. Chem., Int. Ed.. 2004, 43, 4349-4352.

39 Exploring New Uses for C-H Amination: Ni-Catalyzed Cross-Coupling of Cyclic Sulfamates Wehn, P. M.; J. J.; Du Bois, J. Org. Lett. 2005, 7, 4685-4688.

40 Exploring New Uses for C-H Amination: Ni-Catalyzed Cross-Coupling of Cyclic Sulfamates Wehn, P. M.; J. J.; Du Bois, J. Org. Lett. 2005, 7, 4685-4688.

41 Exploring New Uses for C-H Amination: Ni-Catalyzed Cross-Coupling of Cyclic Sulfamates Wehn, P. M.; J. J.; Du Bois, J. Org. Lett. 2005, 7, 4685-4688.

42 Exploring New Uses for C-H Amination: Ni-Catalyzed Cross-Coupling of Cyclic Sulfamates Wehn, P. M.; J. J.; Du Bois, J. Org. Lett. 2005, 7, 4685-4688.

43 Exploring New Uses for C-H Amination: Ni-Catalyzed Cross-Coupling of Cyclic Sulfamates Wehn, P. M.; J. J.; Du Bois, J. Org. Lett. 2005, 7, 4685-4688.

44 Oxaziridine-Mediated Catalytic Hydroxylation of Unactivated 3° C-H Bonds Using Hydrogen Peroxide Brodsky, B. H.; J. J.; Du Bois, J. J. Am. Chem. Soc. 2005, ASAP.

45 Oxaziridine-Mediated Catalytic Hydroxylation of Unactivated 3° C-H Bonds Using Hydrogen Peroxide Brodsky, B. H.; J. J.; Du Bois, J. J. Am. Chem. Soc. 2005, ASAP.

46 Oxaziridine-Mediated Catalytic Hydroxylation of Unactivated 3° C-H Bonds Using Hydrogen Peroxide Brodsky, B. H.; J. J.; Du Bois, J. J. Am. Chem. Soc. 2005, ASAP.

47 Oxaziridine-Mediated Catalytic Hydroxylation of Unactivated 3° C-H Bonds Using Hydrogen Peroxide Brodsky, B. H.; J. J.; Du Bois, J. J. Am. Chem. Soc. 2005, ASAP.

48 Oxaziridine-Mediated Catalytic Hydroxylation of Unactivated 3° C-H Bonds Using Hydrogen Peroxide Brodsky, B. H.; J. J.; Du Bois, J. J. Am. Chem. Soc. 2005, ASAP.

49 Oxaziridine-Mediated Catalytic Hydroxylation of Unactivated 3° C-H Bonds Using Hydrogen Peroxide Brodsky, B. H.; J. J.; Du Bois, J. J. Am. Chem. Soc. 2005, ASAP.

50 A Stereoselective Synthesis of (-)-Tetrodotoxin Hinman, A.; J. J.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511.

51 A Stereoselective Synthesis of (-)-Tetrodotoxin Hinman, A.; J. J.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511.

52 A Stereoselective Synthesis of (-)-Tetrodotoxin Hinman, A.; J. J.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511.

53 A Stereoselective Synthesis of (-)-Tetrodotoxin Hinman, A.; J. J.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511.

54 A Stereoselective Synthesis of (-)-Tetrodotoxin Hinman, A.; J. J.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511.

55 A Stereoselective Synthesis of (-)-Tetrodotoxin Hinman, A.; J. J.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511.


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