Sample Courses
- Organic Chemistry 1
- Organic Chemistry 2
- Mechanistic Organic Chemistry
- Biochemistry
- Chemistry of Food
Research
The Scullab is an organic methodology group focused on the chemical synthesis of phosphates and other biomimetics. Phosphates are a ubiquitous functional group within biological systems that are incorporated in critical molecules such as DNA, RNA, proteins and small molecule messengers such as ATP and inositol phosphates. The development of new and more efficient methods for forming phosphorylated compounds can impact the treatment of diseases where phosphorylation is aberrant (such as cancer), initiate the use of phosphorylated small molecules in disease treatment and answer fundamental questions about the nature of this chemical structure.
Research in our group focuses on the development of new methods to phosphorylate alcohols utilizing both phosphorous (III) and phosphorous (V) reagents. Key questions for our lab are:
- What is the phosphate source?
- What catalysts are effective?
- What protecting groups can we use on phosphorus?
- If two or more hydroxyl groups are present, how do we selectively phosphorylate just one?
Publications
(19) “Catalyst identification for chemoselective phosphorylation of phenols and aliphatic alcohols” E.M. Eason*, W.J. Reller*, Katerine R. Fazekas*, B.R. Sculimbrene Tetrahedron Lett. 2023, 129, 154680.
(18) “Desymmetrization of Diols by Phosphorylation with a Titanium-BINOLate Catalyst” E.T. Ouellette, M.G. Lougee, A.R. Bucknam, P.J. Endres, J.Y. Kim, E.J. Lynch, E.J. Sisko, B.R. Sculimbrene, J. Org. Chem. 2021, 86, 7450-7459.
(17) “Outer-Sphere Control for Divergent Multicatalysis with Common Catalytic Moieties” C.R. Shugrue, B.R. Sculimbrene, E.R. Jarvo, S.J. Miller J. Org. Chem. 2019, 84, 1664-1672.
(16) "Synthesis of alpha-chiral-beta,gamma-unsaturated carboxylic acid derivatives using chiral auxiliaries" K.E. Poremba, V.A. Lee, B.R. Sculimbrene Tetrahedron, 2014, 70, 5463-5467.
(15) "Selective Phosphorylation of Diols with a Lewis Acid Catalyst" K.A. Coppola, J.W. Testa, E.E. Allen, and B.R. Sculimbrene Tetrahedron Lett. 2014, 55, 4203-4206.
(14) "Catalytic Lewis Acid Phosphorylation with Pyrophosphates" O.S. Fenton, E.E. Allen, K.P. Pedretty, S.D. Till, J.E. Todaro and B.R. Sculimbrene Tetrahedron, 2012, 68, 9023-9028.