Our research program is focussed on the development of new synthetic methods using organoboron compounds and reactive intermediates. These methods are being applied to the synthesis of biologically active natural products, such as N-heterocyclic natural products and guanidine containing compounds. In addition we are developing new reagents and reactions that can be applied for combinatorial chemistry.
The addition of aryl, alkenyl and alkyl organometallic species such as organolithium and Grignard reagents to carbonyl groups is arguably the most important C-C bond forming reaction in organic chemistry. This reaction suffers from two main limitations however, (i) no control of enantioselectivity and (ii) a lack of stability of these reagents to air, water and heat. We are working on organoboron alternatives to organolithium and Grignard reagents, and have had considerable recent successes in achieving additions of alkenyl and aryl boron reagents using transition metal catalysis. This methodology is expected to be of considerable utility for use in combinatorial synthesis. In addition, we have shown that potassium allyl and crotyl trifluoroborates, as highly reactive reagents for diastereoselective additions to aldehydes, ketones and other electrophilic species.