Trimethylsilyl trifluoromethanesulfonate as a metal-free, homogeneous, strong Lewis acid catalyst for efficient one pot synthesis of α-aminonitriles and their fluorinated analogs

ORGN 46

G. K. S. Prakash, gprakash@usc.edu, Chiradeep Panja, chiradep@usc.edu, Clement Do, Thomas Mathew, tmathew@usc.edu, and George A. Olah, olah@usc.edu. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, CA 90089-1661
α-Aminonitriles and their fluorinated analogs are important classes of compounds, which show interesting pharmaceutical and biological properties. They are also the precursors of the corresponding amino acids. Presence of fluorine atom increases their biological activities significantly. However, metal based reagents and catalyst used to synthesize such types of compounds are often not desired in pharmaceutical industries. Trimethylsilyl trifluoromethanesulfonate (TMS-OTf) is found to be an efficient strong, homogeneous and metal-free Lewis acid system for various synthetic transformations. A successful one pot three component Strecker reaction of ketones/fluorinated ketones has been achieved using TMS-OTf as a strong Lewis acid catalyst. These reactions are simple, clean and minimal work up-purification steps are required. Products are obtained in high yield and high purity. Monofluoro, difluro or trifluoromethyl groups can be incorporated into the α-aminonitrile product by varying the nature of the fluorinated ketones.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Sunday, August 19, 2007 BCEC -- 258B, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007