Reaction Methodology Utilizing Chiral Phosphate
Derived Catalysts
Jon C. Antilla*
University of South Florida, Department of Chemistry, 4202 E Fowler Ave, Tampa, Florida, 33620 USA
Email: jantilla@usf.edu
Organocatalysis is considered by many to be an attractive, and potential “green” alternative to
traditional metal-based catalysis. This research specifically seeks to develop new reaction methodologies
that utilize chiral phosphoric acids as functional asymmetric organocatalysts for synthetically useful
transformations. Another way to utilize chiral phosphoric acids is to use them as a starting point to form
new chiral organocatalysts or even metal catalysts with phosphate ligands. Our initial discoveries and our
most recent developments that allow for the asymmetric allylation and propargylation of aldehydes will be
highlighted. In addition I will discuss the use of chiral phosphoric acid derived catalysts for use in the
enantioselective reduction of ketones and also show a highlight of our work in synthesis.
OH
O
H
+
O
B
(R)-TRIP-PA (5 mol %)
O
solvent, rt
99% yield
97% ee
Fig. 1
(1). Jain, P.; Antilla, J. C. J. Am. Chem. Soc. 2010, 132, 1184.
(2). Zhang, Z.; Antilla, J. C. Angew. Chem. Int. Ed. 2012, 51, 11778.
(3). Jain, P.; Wang, H.; Houk, K. N.; Antilla, J. C. Angew. Chem. Int. Ed. 2012, 51, 1391.
Jon Antilla graduated from Northern Michigan University in 1995 and received his PhD in
2000 from The University of Chicago with William D. Wulff. His postdoctoral studies were with
Stephen L. Buchwald at MIT from 200-2003. His first independent position was at The University of
Mississippi as an Assistant Professor. He then moved to The University of South Florida in 2006. He
has been promoted to Associate Professor of Chemistry in 2010. He is a recipient of a NSF
CAREER award in 2009 and has been a Visiting Professor at University of Le Havre in France in
2009, a Visiting Professor at Jilin University since 2010, and a JSPS Scholar in Japan in 2011. His
current research interests are centered on the use of chiral phosphoric acids as organocatalysts for
new reaction methodology. He is also interested in the use of chiral phosphates as ligands for
metal-catalyzed reactions for enantiocontrolled bond formations.