Publication details

Benzoin as a photoremovable chiral auxiliary


KAMMATH Viju Balachandran ŠEBEJ Peter SLANINA Tomáš KLÁN Petr

Year of publication 2009
Type Article in Proceedings
Conference 238th American Chemical Society National Meeting & Exposition
MU Faculty or unit

Faculty of Science

Field Organic chemistry
Keywords Benzoin; Chiral Auxiliary; Photochemistry; Photoremovable Protecting Group; Diels-Alder Reaction
Description Controlling the reaction stereochemistry is often achieved by using a chiral auxiliary which is covalently attached to the prochiral substrate before chirality relay is performed. These groups are optically active compounds or units that are temporarily incorporated to be utilized in the selective formation of one of the enantiomers. Here photoremovable chiral auxiliary (PCA) represents a new strategy in the field of asymmetric organic synthesis, which offers a chiral auxiliary that can be photochemically removed under specific conditions. The benzoin group is known to be a good photoremovable protecting group for a variety of functionalities, such as carboxylates, hydroxyls, phosphates etc. Since benzoin contains a chiral center, we proposed and studied its derivatives as PCA. Enantiopure benzoin group is connected to a dienophile which reacts with a diene in the presence of various catalysts. The auxiliary is then removed upon irradiation giving the products exhibiting enantiomeric excess.
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