研究领域

Organic Chemistry Organometallic Chemistry Complex Molecule Synthesis

Our research program focuses on the discovery of new transition metal-catalyzed reactions, the development of useful synthetic methods, the application of these new reactions in complex molecule synthesis, and mechanistic studies designed to understand the new processes developed in our laboratories. A major focus of our research program in recent years has been the development of new reactions involving nickel catalysis. In particular, our lab has discovered a series of new reactions that involve the reductive coupling of two different unsaturated moieties in a Ni(0)-catalyzed process. A broad range of pi-systems, including aldehydes, enones, alkynes, allenes, and dienes, are effective participants in this group of reactions. The challenges addressed by the new reactions being developed in our group include the stereoselective introduction of exocyclic double bonds and the stereoselective preparation of polycyclic ring systems that possess multiple contiguous stereocenters. Precise control of catalyst structure and reaction conditions allows a wide array of reaction pathways to be accessed from simple, readily available starting materials. A variety of natural products have been synthesized in our laboratories using these methods, including isodomoic acids G and H, allopumiliotoxins 339A and 339B, and testudinariol A. We have recently discovered a new three-component cycloaddition reaction for the synthesis of complex seven-membered rings by a [4+2+1] cycloaddition pathway involving diazoalkanes, alkynes, and dienes. We are actively pursuing the development of new cycloaddition processes based on the novel reactivities uncovered, and we plan to develop applications of these new reactions in complex molecule total synthesis. A third area of interest is the discovery of new three-component coupling processes involving conjugate addition strategies that avoid the use of metallated nucleophiles. The sensitive nature of organocuprates often limits their utility in synthesis, and we have initiated a program to allow stable and commercially available aryl iodides to be directly utilized in conjugate additions.

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Wang, H.; Negretti, S.; Knauff, A. R.; Montgomery, J. "Exo-Selective Reductive Macrocyclization of Ynals" Org. Lett. 2015, In Press. (Link) Jackson, E. P.; Montgomery, J. "Regiocontrol in Catalytic Reductive Couplings through Alterations of Silane Rate Dependence" J. Am. Chem. Soc. 2015, 137, 958-963. (Link) Haynes, M. T.; Liu P.; Baxter, R. D.; Nett, A. J.; Houk, K. N.; Montgomery, J. "Dimer Involvement and Origin of Crossover in Nickel-Catalyzed Aldehyde-Alkyne Reductive Couplings" J. Am. Chem. Soc. 2014, 136, 17495-17504. (PDF) Miller, Z. D.; Montgomery, J. "Regioselective Allene Hydroarylation via One-Pot Allene Hydrosilylation/Pd-Catalyzed Cross-Coupling" Org. Lett. 2014, 16, 5486-5489. (Link) Haynes, M. T.; Jackson, E. P.; Montgomery, J. "Nickel Complexes of N-Heterocyclic Carbenes" in N-Heterocyclic Carbenes: Effective Tools for Organometallic Synthesis Nolan, S. P. (Ed.) Wiley-VCH 2014, pp. 371-496. (Link) Negretti, S.; Narayan, A.R.H.; Chiou, K.C.; Kells, P.M.; Stachowski, J.L.; Hansen, D.A.; Podust, L.M.; Montgomery, J.; Sherman, D.H. "Directing Group-Controlled Regioselectivity in an Enzymatic C–H Bond Oxygenation" J. Am. Chem. Soc. 2014, 136, 4901-4904. (Link) Montgomery, J. "Organonickel Chemistry" in Organometallics in Synthesis: Fourth Manual Lipshutz, B. H. (Ed.) Wiley, Hoboken, N.J., 2013, pp. 319-428. (Link) Partridge, K.M.; Bader, S.J.; Buchan, Z.A.; Taylor, C.E.; Montgomery, J. "A Streamlined Strategy for Aglycone Assembly and Glycosylation" Angew. Chem. Int. Ed., 2013, 52, 13647-13650. (Link) Miller, Z.D.; Li, W.; Belderrain, T.R.; Montgomery, J. "Regioselective Allene Hydrosilylation Catalyzed by N-Heterocyclic Carbene Complexes of Nickel and Palladium" J. Am. Chem. Soc., 2013, 135, 15282-15285. (Link) Lage, M. L.; Bader, S. J.; Sa-ei, K.; Montgomery, J. "Chemoselective Hydrosilylation of Hydroxyketones" Tetrahedron, 2013, 69, 5609-5613. (Link) Shareef, A.R.; Sherman, D.H.; Montgomery, J. "Nickel-Catalyzed Regiodivergent Approach to Macrolide Motifs" Chem. Sci., 2012, 3 (3), 892-895. (Link) Li, Wei; Montgomery, J. "Ligand-Guided Pathway Selection in Nickel-Catalyzed Couplings of Enals and Alkynes" Chem. Commun., 2012, 48 (8), 1114-1116. (Link) Montgomery, J. "High-Throughput Discovery of New Chemical Reactions" Science, 2011, 333, 1387-1388. (Link) Jenkins, A. D.; Herath, A.; Song, M.; Montgomery, J. "Synthesis of Cyclopentenols and Cyclopentenones via Nickel-Catalyzed Reductive Cycloaddition" J. Am. Chem. Soc., 2011, 133 (36), 14460-14466. (Link) Thompson, B. B., Montgomery, J. "Enone-Alkyne Reductive Coupling: A Versatile Entry to Substituted Pyrroles" Org. Lett., 2011, 13 (13), 3289-3291. (Link) El Douhaibi, A.S.; Kassab, R.M.; Song, M.; Montgomery, J. "Nickel-Catalyzed Cyclizations of Enoates and Chiral Allenes: An Approach to Domoic Acid" Chem. Eur. J., 2011, 17, 6326-6329. (Link) Liu, P.; Montgomery, J.; Houk, K.N. "Ligand Steric Contours to Understand the Effects of N-Heterocyclic Carbene Ligands on the Reversal of Regioselectivity in Ni-Catalyzed Reductive Couplings of Alkynes and Aldehydes" J. Am. Chem. Soc, 2011, 133 (18), 6956-6959. (Link) Baxter, R.D.; Montgomery, J. "Mechanistic Study of Nickel-Catalyzed Ynal Reductive Cyclizations through Kinetic Analysis" J. Am. Chem. Soc., 2011, 133 (15), 5728-5731. (Link) Li, W.; Chen, N. Montgomery, J. "Regioselective Nickel-Catalyzed Reductive Couplings of Enones and Allenes" Angew. Chem. Int. Ed.., 2010, 49, 8712-8716. (Link) Phillips, J. H.; Montgomery, J. "Mechanistic Insights into Nickel-Catalyzed Cycloisomerizations" Org. Lett., 2010, 12, 4556-4559. (Link)