With this CAREER award, the Chemical Synthesis program is supporting the research of Professor Issac Krauss at Brandeis University. Professor Krauss will develop cyclopropanated allylboronate reagents and catalysts which can be used for diastereo- and enantioselective homoallylation and homocrotylation of aldehydes and related electrophiles. In the reagent development area, Dr. Krauss will 1) explore homoallylation scope and diastereoselection with variously substituted racemic boronates, 2) investigate enantioselection and matched/mismatched effects with alpha-chiral boronates, 3) develop optimal syntheses of optically active trans boronates for enantioselective syn homocrotylation and optically active cis- and trisubstituted boronates for enantioselective anti homocrotylation and delivery of quaternary stereocenters, and 4) demonstrate the utility of these boronates in a concise formal synthesis of spongidepsin. In the catalyst development area, Dr. Krauss will explore the potential chiral and achiral homoallylation catalysis by 1) boron carboxylates, 2) boron phenolates, and 3) other Lewis acids, combined with O,O-, N,O-, and N,N-boracycle reagents. Finally, in collaboration with Professor Kendall N. Houk's group at UCLA, computational studies will assist in catalyst and boronate design.
This project focuses on the development of more efficient methods for the preparation of complex organic molecules. Since most medicines and pesticides are made of complex organic molecules, more efficient preparation methods will facilitate the development of new medicines and pesticides. They could also improve the current preparation of existing medicines and pesticides, thus lowering their costs. Synthesis of complex organic molecules are also required in many other areas of activities such as advanced material preparations and fundamental biological studies. In addition, Professor Krauss will develop an educational program to increase scientific literacy in mature citizens. With the support of BOLLI (Brandeis' Osher Lifelong Learning Institute) a series of lay-appropriate educational presentations and seminars will promote scientific literacy and highlight the impact of basic research in everyday life. Design and execution of these presentations will include graduate participation. Presentations and seminars piloted as BOLLI programming will also be repeated at Boston area retirement communities and posted on the web.
