Office: 405 Coulter Hall
Email: tomioka AT olemiss.edu
Educational and Professional Background
B.S., Nagoya University (Japan), 1998
Ph.D., University of California, Santa Barbara, 2004
Postdoctral Fellow, University of Pennsylvania, 2004-2006
Research Interests: Synthetic Organic Chemistry
Our research program is broadly defined as synthetic organic chemistry, including synthetic methodology, organometallic chemistry, and natural/unnatural product synthesis. Current major interest is developing/discovering new synthetic tools (method, reagent, concept, etc), which could be utilized for further practical applications towards total synthesis, medicinal chemistry, and material sciences. One of our research plans is briefly described below.
Development of Novel Multi-Functionalizing Reagent:
Introducing and/or transforming functionalities on organic molecules are the most fundamental, as well as crucial technologies for synthetic chemists. Along with the continuous evolution of organic chemistry and the related interdisciplinary fields, our study targets are becoming more complex and broader, which eventually require many complicated multi-step reactions. One step or one pot multi-functionalization is, therefore, one of the ideal solutions to easily access a variety of molecules (Figure 1). Our conceptual goal is to develop a densely multi-functionalized reagent for efficient poly-functionalization without sacrificing/wasting either functionality, ultimately offering (1) short reaction steps, (2) high atom efficiency, (3) good cost performance, (4) less chemical wastes, and (5) wide synthetic applicability.
Among the various possibilities, we are particularly interested in boron functionality. Since the discovery of Suzuki coupling reaction and the broad recognition of its powerful utility, especially for C-C bond formations, the demand of organoboron compounds has increased explosively over the last decade in both industry and academia. Cyclic pinacol type ester of boronic acid is particularly a useful organoboron species for Suzuki reaction. However, the number of practical pathways to install such boronate moieties is still limited. Moreover these conditions are typically functional group sensitive. Therefore, an alternate method introducing a boronate ester with additional functionalities on a molecule utilizing a uniquely designed bifunctional reagent would be highly desirable. The extensive study of its synthetic scope and limitation under various organic reactions would enable us to supply novel multi-purpose reagents for the organic community.
Tomioka, T.*; Takahashi, Y.; Maejima, T. "One-pot synthesis of 2-aminoquinoline-based alkaloids from acetonitrile", Org. Biomol. Chem. 2012
Tomioka, T.*; Sankranti, R.; Vaughan, T. G.; Maejima, T.; Yanase, T. "An α-Diaminoboryl Carbanion Assisted Stereoselective Single-Pot Preparation of α,β-Disubstituted Acrylonitriles", J. Org. Chem. 2011
, 76, 8053-8058.
Tomioka, T.*; Yabe, Y.; Takahashi, T.; Simmons, K. T. "DIBAL-Mediated Reductive Transformation of trans-Dimethyl Tartrate Acetonide into ε-Hydroxy α,β-Unsaturated Ester and Its Derivatives", J. Org. Chem. 2011
, 76, 4669-4674.
Tsuda, T.*; Kondo, K.; Tomioka, T.*; Takahashi, Y.; Matsumoto, H.; Kuwabata, S.; Hussey, C. L. “Design, Synthesis, and Electrochemistry of Functionalized Room-Temperature Ionic Liquids with Propylene Carbonate”, Angew. Chem. Int. Ed. 2011
, 50, 1310. [Selected as a ‘hot’ paper by the Editors.]
Tomioka, T.*; Takahashi, Y.; Vaughan, T. G.; Yanase, T. “A Facile, One-Pot Synthesis of β-Substituted (Z)-Acrylonitriles Utilizing an α-Diaminoboryl Carbanion”, Org. Lett. 2010
, 12, 2171-2173. [Highlighted in SYNFACTS, 2010, 8, 931.]
Smith, A. B., III*; Sfouggatakis, C.; Risatti, C. A.; Sperry, J. B.; Zhu, W.; Doughty, V. A.; Tomioka, T.; Gotchev, D. B.; Bennett, C. S.; Sakamoto, S.; Atasoylu, O.; Shirakami, S.; Bauer, D.; Takeuchi, M.; Koyanagi, J.; Sakamoto, Y. “Spongipyran Synthetic Studies. Evolution of a Scalable Total Synthesis of (+)-Spongistatin 1”, Tetrahedron 2009
, 65, 6489-6509.
Tsuda, T.; Tomioka, T.; Hussey, C.L.* “Physicochemical Properties of Highly Conductive Urea−EtMeImCl Melts.” Chem. Commun. 2008
Smith, A.B.,III*; Tomioka, T; Risatti, C.A.; Sperry, J.B.; Sfouggatakis C. "Gram-Scale Synthesis of (+)-Spongistatin 1: Development of An Improved, Scalable Synthesis of the F-Ring Subunit, Fragment Union, and Final Elaboration" Org. Lett. 2008
, 10, 4359-4362.
Nomura, N.; Taira, A.; Nakase, A.; Tomioka, T.; Okada, M.* “Ring-opening polymerization of lactones by rare-earth metal triflates and their reusable system in ionic liquids.” Tetrahedron 2007
, 63, 8478-8484.