Educational Background

B.A./M.A., Boston University, 1996

Ph.D., The University of Chicago, 2002

Professional Experience

Associate Professor, Florida Institute of Technology, 2015 —

Visiting Associate Professor, Florida Institute of Technology, 2014-2015

Assistant Professor, University of Miami, 2005-2014

Postdoctoral Fellow, University of Chicago, 2002-2005

Current Courses

I teach Organic Chemistry courses (CHM2001 & 2002) and Advanced Organic Chemistry course (CHM5500).

Teaching Philosophy

My enthusiasm and vigor to pursue an academic career stem from a nearly balanced will to conduct research at the cutting edge of organic chemistry and to foster the next generation of scientists at all levels who will contribute to our society.  Organic chemistry has, and will continue to have an enormous impact on fine chemical synthesis and, more broadly, on the fields that rely upon the availability of small organic molecules (e.g., biology and human medicine).  Therefore, the study of organic chemistry is a critical endeavor for students who wish to pursue any of these fields in greater depth.  The development of educational programs that lead students to a firm foundation in the sciences and specifically the chemical science is of national interest.  The basic science courses at both undergraduate and graduate levels, and the research training in the laboratory are vital components of such scientific education. To this goal, by teaching courses and conducting the cutting-edge research, I aim; (1) to enlighten the importance of science education among the undergraduates, particularly freshman and sophomore students (recent studies show that the majority of scientists and graduate students report becoming interested in their career discipline during early stages in college), (2) to foster the scientific development of students at all levels, and (3) to promote careers in the sciences. I strongly believe that the courses that focus on the fundamentals are very important because understanding them allows students to bind together the major disciplines of molecular science. The research training reinforces those learning thus lead students to a firm foundation in the sciences.

Selected Publications

Independent Publications

27)       Changgong Xu, Phillip Nader, Jonathan Xavier, Norito Takenaka “Asymmetric Allenylation of N-Acylhydrazones with Propargyltrichlorosilane Catalyzed by Helical Chiral 2,2’-Bipyridine N-monoxide” Synlett, 2023, 34, 2461-2464.

 26)       Changgong Xu, Phillip Nader, Jonathan Xavier, Burjor Captain, Norito Takenaka “Evaluation of helicene-derived 2,2’-bipyridine N-monoxide catalyst for the enantioselective propargylation of N-acylhydrazones with allenyltrichlorosilane” Tetrahedron, 2023, 141, 133496. (This work was selected as part of Tetrahedron 2023 Editors’ Choice Collection.)

 25)       Shishir Chourey, Rui Wang, Qiuji Ye, Chintam Nagendra Reddy, Shiyu Sun, Norito Takenaka, William S. Powell, and Joshua Rokach, “Concise Synthesis of Micirosomal Metabolites of a Potent OXE (Oxoeicosanoid) Receptor Antagonist” Chem. Pharm. Bull. 2023, 71, 534-544.

24)       Morgante, P.; Deluca, C.; Jones, T. E.; Aldrich, G. J.; Takenaka, N.*; Peverati, R.*  “Steps Towards Rationalization of the Enantiomeric Excess of the Sakurai-Hosomi-Denmark Allylation Catalyzed by Biisoquinoline N,N’-Dioxides Using Computations” Catalysts 2021, 11, 1487. 

23)       Sun, S.; Xu, C.; Jarvis, J.; Nader, P.; Naumann, B.; Soliven, A.; Peverati, R.*; Takenaka, N.* “Evaluation of 3,3’-Triazolyl Biisoquinoline N,N’-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane” Catalysts 2021, 11, 1103.

22)       Sun, S.; Reep, C.; Zhang, C.; Captain, B.; Peverati, R.*; Takenaka, N.* “Design and synthesis of 3,3’-triazolyl biisoquinoline N,N’-dioxides via Hiyama cross-coupling of 4-trimethylsilyl-1,2,3-triazoles” Tetrahedron Letters2021, 81, 153338.

21)       Xu, C.; Reep, C.; Jarvis, J.; Naumann, B.; Captain, B.; Takenaka, N.* “Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations” Catalysts 2021, 11, 712-759.

20)       Morgante, P.; Captain, B.; Chouinard, C. D.; Peverati, R.*; Takenaka, N.* “Synthesis of electrophilic N-heterocyclic carbenes based on azahelicene” Tetrahedron Letters 2020, 61, 152143.

19)       Reep, C.; Sun, S.; Takenaka, N.*, “C(sp²)–H Hydrogen-Bond Donor Groups in Chiral Small-Molecule Organocatalysts” Asian Journal of Organic Chemistry 2019, 8, 1306-1316.

18)       Reep, C.; Morgante, P.; Peverati, R.*; Takenaka, N.*, “Axial-Chiral Biisoquinoline N,N’-Dioxides Bearing Polar Aromatic C–H Bonds as Catalysts in Sakurai-Hosomi-Denmark Allylation” Organic Letters 2018, 20, 5757-5761.

17) Narcis, M. J.; Takenaka, N. “Helical-Chiral Small Molecules in Asymmetric Catalysis” Eur. J. Org. Chem., 2014, 21-34. (This work was among the 25 most accessed articles of the year.)

16) Peng, Z.; Narcis, M. J.; Takenaka, N. “Enantio- and Periselective Nitroalkene Diels-Alder Reactions Catalyzed by Helical-Chiral Hydrogen Bond Donor Catalysts” Molecules, 2013, 18, 9982-9998.

15) Peng, Z.; Takenaka, N. “Application of Helical-Chiral Pyridines as Organocatalysts in Asymmetric Synthesis” The Chemical Record, 2013, 13, 28- 42.

14) Narcis, M. J.; Sprague, D. J.; Captain, B.; Takenaka, N. “Enantio- and periselective nitroalkene Diels-Alder reaction” Org. Biomol. Chem., 2012, 10, 9134-9136.

13) Chen, J.; Captain, B.; Takenaka, N. “Helical Chiral 2,2’-Bipyridine N-Monoxides as Catalysts in the Enantioselective Propargylation of Aldehydes with Allenyltrichlorosilane” Org. Lett., 2011, 13, 1654-1657.

12) Aguado, A.; Takenaka, N. “Intramolecular Nitroalkene Diels-Alder Reaction Catalyzed by Brønsted Acids” Synlett, 2011, 9, 1259-1261.

11) Takenaka, N.; Chen, J.; Captain, B.; Sarangthem, R. S.; Chandrakumar, A. “Helical Chiral 2-Aminopyridinium Ions: A New Class of Hydrogen Bond Donor Catalysts” J. Am. Chem. Soc. 2010, 132, 4536-4537. (Highlighted in Synfact 2010, 6, 712.)

10) Chen, J.; Takenaka, N. “Helical Chiral Pyridine N-Oxides: A New Family of Asymmetric Catalysts” Chem. Eur. J. 2009, 15, 7268-7276.

9) Takenaka, N.; Sarangthem, R. S.; Captain, B. “Helical-Chiral Pyridine N-Oxides, a New Family of Asymmetric Catalysts” Angew. Chem. Int. Ed. 2008, 47, 9708- 9710. (This work was among the 12 most accessed articles of the month.)

8) Takenaka, N.; Sarangthem, R. S.; Seerla, S. K. “2-Aminopyridinium Ions Activate Nitroalkenes through Hydrogen Bonding” Org. Lett., 2007, 9, 2819- 2822.

Undergraduate, Graduate and Postdoctoral Publications

7) Takenaka, N.; Abel, J. P.; Yamamoto, H. “Asymmetric Conjugate Addition of Silyl Enol Ethers Catalyzed by Tethered Bis(8-Quinolinolato) Aluminum Complexes” J. Am. Chem. Soc. 2007, 129, 742-743.

6) Unni, A. K.; Takenaka, N.; Yamamoto, H.; Rawal, V. H. “Axially Chiral Biaryl Diols Catalyze Highly Enantioselective Hetero-Diels-Alder Reactions through Hydrogen Bonding” J. Am. Chem. Soc. 2005, 127, 1336-1337.

5) Takenaka, N.; Xia, G.; Yamamoto, H. “Catalytic, Highly Enantio- and Diastereoselective Pinacol Coupling Reaction with a New Tethered Bis(8- quinolinolato) Ligand” J. Am. Chem. Soc. 2004, 126, 13198-13199.

4) Takenaka, N.; Huang, Y.; Rawal, V. H. “The First Catalytic Enantioselective Diels-Alder Reactions of 1,2-Dihydropyridine: Efficient Syntheses of Optically Active 2-Azabicyclo-[2.2.2]octanes with Chiral BINAM Derived Cr (III) Salen Complexes” Tetrahedron, 2002, 58, 8299-8305.

3) Hu, T.; Takenaka, N.; Panek, J. S. “Asymmetric Crotylation Reactions in the Synthesis of Polypropionate Derived Macrolide: Application to the Total Synthesis of Oleandolide” J. Am. Chem. Soc. 2002, 124, 12806-12815.

2) Hu, T.; Takenaka, N.; Panek, J. S. “Total Synthesis of Oleandolide” J. Am. Chem. Soc. 1999, 121, 9229-9230.

1) Jain, N. F.; Takenaka, N.; Panek, J. S. “Double-Stereodifferentiating Crotylation Reactions with Chiral (E)-Crotylsilanes. Evaluation of a New Approach for the Synthesis of Polypropionate-Derived Natural Products” J. Am. Chem. Soc. 1996, 118, 12475-12476.

Recognition & Awards

AWARDS and HONORS

2008, Thieme Chemistry Journals Award (Germany)

2007, University of Miami Provost Award

2006, Summer Award in the Natural Sciences and Engineering, University of Miami

2006, University of Miami Provost Award

GRANTS and CONTRACTS

2020-2024, National Institute of Health, NIGMS

2012-2016, National Science Foundation, Chemical Synthesis Program

2007-2010, James and Esther King Biomedical Research Program

2007-2008, American Cancer Society IRG

Research

Research Interests

The Takenaka group is interested in synthetic organic chemistry in broad terms, which range from asymmetric catalysis to synthesis of complex natural products. New methods offer new ways to assemble the complex molecular architecture and execution of resulting new synthetic strategies, in turn, lead to new insights and discoveries in method development. Methodology and synthesis are expected to complement to each other. The group’s focus is on the design and development of conceptually new catalysts for the promotion of selective chemical transformations of broad synthetic utility. Of particular interest is the development of environmentally benign, highly versatile Lewis/Brønsted acids that catalyze carbon-carbon bond formation with the highest level of selectivity and efficiency, which is of central importance in organic synthesis. The second major focus of our program is on the synthesis of structurally interesting and biologically significant natural products that not only encompass our own synthetic methods but also inspire further methodology and strategy development, including mechanistic aspects. The objectives of such endeavors are the discovery and development of new synthetic technology that provides efficient access to potential pharmaceuticals in green, non-toxic fashion, as well as better understanding of organic chemistry.

Development of New Organocatalysis Methods

Drug therapy is among the most successful and reliable treatments for various health issues. However, it is impeded by limitations in chemists’ ability to make the absolutely “correct” drug molecule in a timely and cost-effective manner. Asymmetric organocatalysis is a new approach in chemistry dedicated to the preparation of molecules with defined 3-D structure (molecular shape), and is of paramount importance to the drug discovery and development because the function of a drug is determined by its overall shape.

Researchers in the Takenaka Lab have developed a new class of organocatalysts that shape-selectively synthesize molecules with the desired 3-D structure from readily available chemicals. Such technology will provide scientists ready access to precious medicinally active agents, and thus will not only accelerate the drug discovery process, but also lower costs of prescription drugs.

Synthesis of Natural Products

Natural products are the secondary metabolites (small organic molecules) produced in organisms and have long been the source of the great majority of drugs and drug candidates. Indeed, 78% of the antibacterial compounds and 74% of anticancer agents available today are either natural products or their chemical derivatives. The complete chemical synthesis of natural products is the first and key step in such drug discovery endeavors that aim to treat currently incurable diseases.

The researchers in the Takenaka Lab are currently working toward the complete chemical synthesis of the alkaloid Acutumine isolated from the moonseed Sinomenium acutum.