Catalytic Reductive Coupling Reactions - Michigan State University

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<strong>Reductive</strong> <strong>Coupling</strong>s of Allenes and AldehydesHR 1HR 2HOArR 3 SiHcat. Ni(COD) 2NHC-iPr (1)THFR 1OSiR 3R 2Ari-Pr i-PrN Ni-Pr i-PrNHC-iPr (1)entry allene productallylic:homoallyicyield (allylic)Z / Esiteselectivityee(%)H H1n-Prn-Prn-PrOSiEt 3n-Pr94 : 680%>95:5NA 952HCyHMeOSiEt 3Me93 : 776%>95:5>95:5 98Ng, S-S.; Jamison, T. J. Am. Chem. Soc. 2005, 127, 7320—7321.
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 24 and 25: Proposed Coupling SchemeCyHHMeHOPhE
Page 26 and 27: Mechanism for Ni-Catalyzed Reductiv
Page 28 and 29: Total Synthesis of Amphidinolide T1
Page 30 and 31: Rh-Catalyzed Intramolecular Alder-E
Page 32 and 33: Intramolecular Halogen ShiftClOOCl1
Page 34 and 35: Mechanism via Oxidative Cyclometall
Page 36 and 37: Total Synthesis of (+)-Blastmycinon
Page 38 and 39: C-C Bond Formation with H2 as Termi
Page 40 and 41: Reductive HydrogenationClPh 3 PRhPP
Page 42 and 43: Addition of Aldehyde Enolates to Ke
Page 44 and 45: Catalytic Cycloreduction Employing
Page 46 and 47: Koech, P.; Krische, M. Org. Lett. 2
Page 48 and 49: Possible Mechanisms for Reductive C
Page 50 and 51: Hydrometallative Catalytic Mechanis
Page 52 and 53: H-D Cross-Over ExperimentsHydrometa
Page 54 and 55: Oxidative Cyclization with Homolyti
Page 56 and 57: Conclusions• Transition-metal cat

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