title: Photoremovable chiral auxiliary.
abstract: A new concept of a photoremovable chiral auxiliary (PCA), based on the chiral benzoin chromophore, is introduced. This moiety can control the asymmetric formation of a Diels-Alder adduct, and then be removed in a subsequent photochemical step in high chemical and quantum yields. Selective formation of the products at up to 96% ee was observed in the presence of a Lewis acid catalyst in the case of a 2-methoxybenzoinyl chiral auxiliary.
authors.affiliation: Department of Chemistry, Faculty of Science, Masaryk University, Brno, Czech Republic.
authors.forename: Viju Balachandran
authors.initials: VB
authors.lastname: Kammath
authors.forename: Peter
authors.initials: P
authors.lastname: Sebej
authors.forename: Tomáš
authors.initials: T
authors.lastname: Slanina
authors.forename: Zdeněk
authors.initials: Z
authors.lastname: Kříž
authors.forename: Petr
authors.initials: P
authors.lastname: Klán
mesh_terms: D001573:Benzoin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010782:Photolysis
chemical_list: D001573:Benzoin