Catalytic Reductive Coupling Reactions - Michigan State University

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Addition of Aldehyde Enolates to KetonesnOO CH 3mOHRh(COD) 2 OTf (10 mol%)(2-furyl) 3 P (24 mol%)H 2 (1 atm)K 2 CO 3 (100 mol%)THF, 40 o CnOOHOCH 3mH1a, n = 1, m = 12a, n = 2, m = 13a, n = 1, m = 21b-4b, Yield %, syn:anti,(Yield % 1,4 Reduction)4a, n = 2, m = 2OOHOCH 3HOOOHCH 3HOHOOCH 3HOHOCHO 3H1b, 72%, 2:1(16%)2b, 73%, 10:1(21%)3b, 63%, 5:1(30%)4b, 59%, 4:1(29%)Koech, P.; Krische, M. Org. Lett. 2004, 6, 691—694.
Proposed Catalytic MechanismOO CH 3OHHHO CH 3ConjugateReductionXLnRh IIIOHOHDi-HydrideCatalytic CycleHLnRh III (H 2 )X-HX (Base)OO CH 3-HX (Base)HXOHLnRh I HConjugate ReductionManifold DisabledOO CH 3LnRh IOHMono-HydrideCatalytic CycleHLnRh IOOHHOCH 3H 3 COOLnRh I XH 2OHOHLn(H) 2 Rh III OOO CH 3HHH 2OHOCH 3Koech, P.; Krische, M. Org. Lett. 2004, 6, 691—694.
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 and 28: 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 39 and 40: Intramolecular Reductive Aldolizati
Page 41: Heterolytic Hydrogen ActivationPh 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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