Studies of chemical reactions of organoboranes

PELLEGRINET, S. C.

Kuala Lumpur

Simposio; International Symposium On Women In Science And Engineering (Wise 2011); 2011

Institut Kimia Malaysia (IKM)

Organoborane compounds are readily available and exhibit low toxicity. In addition, the carbon-boron bond can be easily modified to obtain a variety of chemical functionalities, which makes them very attractive to chemists from the synthetic point of view. We study, design and develop different reactions of organoboranes. The Diels-Alder reaction of boron-activated dienophiles is a useful chemical transformation which yields cyclohexane building blocks. Furthermore, the properties of these dienophiles can be modulated by the rational design of the ligands attached to the boron atom. Dihalovinylboranes and dialkylvinylboranes display exceptional reactivity, regioselectivity and endo-stereoselectivity. On the other hand, vinylboronates exhibit lower reactivity and selectivity but have practical advantages such as higher stability and the possibility to exchange ligands reversibly. Recently, a number of organocatalytic enantioselective addition reactions of different unsaturated boronates have been developed. Organocatalysts include chiral biphenols, a-hydroxyacids and phosphoric acids. This presentation will describe our latest results on the rational design of new Diels-Alder reactions of boron-activated dienophiles. Also, theoretical studies on mechanistically related reactions of unsaturated organoboranes, such as the addition of allylboronates catalyzed by chiral binaphthol-derived phosphoric acids, will be presented.