Catalytic Reductive Coupling Reactions - Michigan State University

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Total Synthesis of Amphidinolide T1 and T4MeMeHO♦OMeOCH 2* *O*MeOO♦nickel-catalyzed alkyne-aldehydereductive coupling (intramolecular)nickel-catalyzed alkyne-epoxidereductive coupling (intermolecular)HO♦MeOCH 2MeOOPhHOMeMePhMePhamphidinolide T1MeMeOOOOMeOH3Me3Me1. Ni(cod) 2 (20 mol%)PBu 3 (40 mol%)Et 3 B, toluene, 60 o CMeColby, E. O’Brien, K.; Jamison, T. J. Am. Chem. Soc. 2005, 127, 4297—4307.OOHPh44%,>10:1 drHOPhMeO2. TBSCl,O imid. TBSO3. O 3 ; Me 2 S31%>10:1 drMe PhOMeOMeOMeMeMeamphidinolide T4Oamphidinolide T1O70%MeOO amphidinolide T474%
Outline• Discovery and Developments ofReductive Coupling Reactions• Pd-catalyzed Reactions• Ni-catalyzed Reactions• Rh-catalyzed Reactions• H2 as Terminal Reductant• Mechanistic Considerations• Conclusions
Page 1 and 2: Catalytic ReductiveCoupling Reactio
Page 3 and 4: Reductive HydrogenationClPh 3 PRhPP
Page 5 and 6: Outline• Discovery and Developmen
Page 7 and 8: Alder-Ene ReactionHXYH Y XHYXHYXX Y
Page 9 and 10: Pd(0)-Catalyzed Couplingsallyl acet
Page 11 and 12: Discovery of Reductive CyclizationE
Page 13 and 14: Screening Pd(2+) CatalystsEEEEcatal
Page 15 and 16: Catalytic Reductive Cyclizationenyn
Page 17 and 18: Pd-Catalyzed CycloisomerizationsnRn
Page 19 and 20: Nickel Catalyzed Coupling Reactions
Page 23 and 24: Reductive Couplings of Allenes and
Page 25 and 26: Ni-Catalyzed Reductive Couplings of
Page 27: Total Synthesis of Amphidinolide T1
Page 31 and 32: Mechanism via Oxidative Cyclometall
Page 33 and 34: Mechanism via Oxidative Cyclometall
Page 35 and 36: Reaction Mechanism via π-Allyl Rho
Page 37 and 38: Outline• Discovery and Developmen
Page 39 and 40: Intramolecular Reductive Aldolizati
Page 41 and 42: Heterolytic Hydrogen ActivationPh 3
Page 43 and 44: Proposed Catalytic MechanismOO CH 3
Page 45 and 46: Reductive Condensation ContinuedOLn
Page 47 and 48: Reductive Condensation ContinuedPre
Page 49 and 50: Reductive Cyclization of DiynesXR 1
Page 51 and 52: Oxidative Cyclization Catalytic Mec
Page 53 and 54: Oxidative Cyclization with Heteroly
Page 55 and 56: Hydrogen-Mediated C-C Bond Formatio
Page 57: Acknowledgments• Dr. Baker• Dr.

Catalytic Reductive Coupling Reactions - Michigan State University

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