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Professor Bakthan Singaram

There are many optically active organic compounds of biological and medicinal significance. For example, statine analogs, antibiotics, anesthetics, heterocyclic compounds, unusual amino acids, and insect pheromones all contain stereogenic centers. There is, therefore, a continuous need for new asymmetric methodology. A major objective of Bakthan Singaram's research program is the development of asymmetric and/or enantioselective methods using organometallic and organoboron compounds. Within this context, an important aspect of his study is to develop novel and efficient chiral auxiliaries and catalysts derived from terpenes, organic acids, and other naturally occurring organic compounds. These compounds are tested for their efficiency in asymmetric reduction and asymmetric allylmetallation reactions. Current emphasis is centered in the areas of organometallics, such as ally and allenyl indium. Another aspect of Dr. Singaram's research involves the development of an optical glucose sensor. Diabetes Mellitus continues to debilitate millions of people worldwide. Although there is no cure for the disease, there are effective ways to manage it. One of the most important ways, involves the monitoring of the blood-glucose levels. Currently, diabetics prick their finger and test the blood three to four times a day. Because glucose levels fluctuate drastically throughout the day, an accurate measure of blood-glucose is difficult. A continuous glucose monitor would thus be of great interest. Research in this area includes the utilization of boronic acid appended viologens for the development of novel fluorescent chemosensors.

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Lacie C Hirayama, Terra D Haddad, Allen G Oliver, Bakthan Singaram
Journal of Organic Chemistry 2012-05-04
We report the first one-pot process for the asymmetric addition of allyl, methallyl, and propargyl groups to aldehydes and ketones using B-chlorodiisopinocampheylborane ((d)DIP-Cl) and indium metal. Under Barbier-type conditions, indium metal was used to generate allyl- and allenylindium intermediates, and subsequent reaction wi...Read More
Terra D Haddad, Lacie C Hirayama, Jannise J Buckley, Bakthan Singaram
Journal of Organic Chemistry 2012-01-20
We report a simple, efficient, and general method for the indium-mediated enantioselective propargylation of aromatic and aliphatic aldehydes under Barbier-type conditions in a one-pot synthesis affording the corresponding chiral alcohol products in very good yield (up to 90%) and enantiomeric excess (up to 95%). The extension o...Read More