Research of chirality is one of the most important subjects in natural sciences. It affects the very biology due to homochirality of life. Single enantiomer products are very important in many everyday appliances, like pharmaceuticals. Synthesis of single enantiomers, or any isomer, products from prochiral species without using expensive enzymes or separating racemates and wasting large portions of the product is long sought by chemist. In physics a breakthrough in research of novel chiral recognition phenomena is taking place and its rapid advance of miniaturized the experimental process from synchrotron to table top devices. Most molecules being used as samples in those experiments are natural plant products such as terpenoids. Terpenoids were chosen to be modified for research of chiral recognition phenomena, mainly the photoelectron circular dichroism. The main aim of this research was to modify sterically hindered terpenoids camphor and fenchone into aryl-imines or azides due to a desirable redshift introduced by inserting such species into the terpene backbone. Camphor reacted in straightforward fashion giving the targeted compounds while fenchone gave mixtures of isomers or in some cases did not react. It was only through reactions of twofold extrusion that fenchone gave targeted products. Discrepancies that arose from different synthetic approaches between two very similar molecules are interesting and elucidate a possibility of steering the reactions toward a targeted isomer by pure chemical means without the use of enzymes or some form of resolution.
Igor Vidanović (Wed,) studied this question.