What is chemoselectivity? Here are some definitions, as well as some examples of reactions involving chemoselectivity. In addition to this definition, we will go over the IUPAC Gold Book. We will also explore the problems of predicting chemoselectivity, and discuss methods for achieving chemoselectivity. Let’s begin! Continue reading to learn more.
IUPAC Gold Book definition
Chemoselectivity refers to the reactivity of a functional group in the presence of other groups. Chemoselectivity is difficult to predict because many plausible reactions lead to different outcomes. Chemoselectivity is the single biggest challenge in the synthesis of complex molecules. Nature has practiced chemoselectivity for billions of years, but chemists have only recently learned how to control it. Chemoselectivity is often caused by functional groups in a molecule, which can unravel a strategic design.
The IUPAC Gold Book was first published more than 30 years ago but is now being updated to reflect our digital age. Dr. Stuart Chalk, Associate Professor of Chemistry at the University of North Florida, is the principal author of the new definition. He is also a titular member of the IUPAC Committee on Publications and Chemical Data Standards. This new version of the definition of chemoselectivity highlights the importance of the chemistry community.
Problems with predicting chemoselectivity
Predicting chemoselectivity is a difficult task. While we can accurately estimate the rate of a reaction by observing the properties of the products, there are many factors that influence the outcome of chemocatalysis. To begin with, we need to understand how chemical reactions operate. Chemoselectivity is defined as the selectivity of a reaction over a series of similar products.
Reactions involving chemoselectivity
The IUPAC defines chemoselectivity as a preferential reaction, and the term embodies the single most difficult barrier to synthesizing a complex molecule. Because nature has mastered this property for billions of years, attempts to make synthetic counterparts of natural products often turn into case studies in chemoselective control. The fact that chemoselectivity is so hard to predict means that chemists must face reactions with functional groups that are either promiscuously reactive or stubbornly inert, which can be equal to the state-of-the-art in stereocontrol.
In addition to its ability to catalyze reactions, the NHC catalyzes the asymmetric desymmetrization of enal-tethered cyclohexadiene. The NHC catalyselectivity involves nucleophilic addition, protonation, and homoenolate intermediate generation. The asymmetric desymmetrization is then followed by esterification. Protonation and esterification are mediated by AcOH. Chemoselectivity is determined by the extent to which these reactions are stereoselective.
Methods to achieve chemoselectivity
Chemoselectivity is an opposition in chemistry that controls the reaction of an organic compound with its target. It is the single largest obstacle to the synthesis of complex molecules, and efforts to produce natural products often become case studies in chemoselectivity. Nature has been a master of this skill for billions of years, so it is no surprise that chemists are now challenged with functional groups that are promiscuously reactive, stubbornly inert or both. Chemoselectivity is the equivalent to the state of the art in stereocontrol.
In some cases, protecting groups are more efficient than chemoselectivity, but this is not the only way to increase the selective power of an organic compound. One example of a protecting group that could enhance chemoselectivity is 4-nitroacetophenone. This compound contains two reducible groups, an aromatic nitro group and an aromatic amine. However, the aromatic nitro group is reduced to an aromatic amine, and the carbonyl group is not reduced.