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 transcript:

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 ( ) (Stephen J. Lippard)

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 , 40,

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 , 40, 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

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 , 40,

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 , 40,

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,

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,

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,

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,

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,

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,

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,

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,

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

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,

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,

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,

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,

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,

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

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

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

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

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

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

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,

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,

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,

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,

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

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 , 43,

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 , 43,

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 , 43,

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 , 43,

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 , 43,

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 , 43,

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 , 43,

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 , 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,

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,

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,

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,

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,

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.

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.

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.

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.

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.

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.

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

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

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

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

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

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