Bodner, R.; Marcellino, B. K.; Severino, A.; Smenton, A. L.; Rojas, C. M.;  α-N Acetylmannosamine (ManNAc) Synthesis via Rhodium(II)-Catalyzed Oxidative Cyclization of Glucal 3-Carbamates, J. Org. Chem. 2005, 70, 3988–3996.

Churchill, D. G.; Rojas, C. M.; Iron(II)-Promoted Amidoglycosylation and Amidochlorination of an Allal C3-Azidoformate, Tetrahedron Lett. 2002, 43, 7225–7228.

Levites-Agababa, E.; Menhaji, E.; Perlson, L. N.; Rojas, C. M.; Amidoglycosylation via Metal-Catalyzed Internal Nitrogen Atom Delivery, Org. Lett. 2002, 4, 863–865.

Kan, C.; Long, C. M.; Paul, M.; Ring, C. M.; Tully, S. E.; Rojas, C. M.; Photo Amidoglycosylation of an Allal Azidoformate.  Synthesis of β-2-Amido Allopyranosides, Org. Lett. 2001, 3, 381–384.

Williams, D. R.; Cortez, G. S.; Bogen, S. L.; Rojas, C. M.; Total Synthesis of Lankacyclinol, Angew. Chem., Int. Ed. 2000, 39, 4612–4615.

Williams, D. R.; Rojas, C. M.; Bogen, S. L.; Studies of Acyl Nitrene Insertions.  A Stereocontrolled Route Toward Lankacidin Antibiotics, J. Org. Chem., 1999, 64, 736–746.

Rojas, C. M.; Rebek, J., Jr.; Convergent Functional Groups.  Intramolecular Acyl Transfer through a 34-Membered Ring, J. Am. Chem. Soc. 1998, 120, 5120–5121.

Invited Chapters

Rojas, C. M.; Zincke Reaction, In Name Reactions in Heterocyclic Chemistry, Li, J. J., Ed.; John Wiley & Sons: New York, NY, 2004, pp 355–375.
 

My research group seeks to develop new methodology for nitrogen atom transfer within complex molecular frameworks.  We have applied these techniques to the preparation of 2-amino sugar derivatives, according to the general scheme shown above.  Internally tethered nitrenes, generated either photochemically or via transition metal catalysis, react with the electron-rich olefin of glycal substrates, leading to formation of a new C-2–N bond and in situ glycosylation with high stereocontrol.  Current work in the group involves extension of this methodology for the preparation of a variety of 2-amino sugar frameworks as well as application to the synthesis of biologically important structures, including the disaccharide portion of the chitinase inhibitor allosamidin, shown below.

In addition to these scientific goals, another key outcome of my program is the involvement of undergraduates in every facet of the research.  The challenge and thrill of making original contributions to organic synthesis provides powerful motivation for Barnard students to pursue graduate training and ultimately careers in the chemical sciences.