Publication details

Photoremovable Chiral Auxiliary

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KAMMATH Viju Balachandran ŠEBEJ Peter SLANINA Tomáš KŘÍŽ Zdeněk KLÁN Petr

Year of publication 2012
Type Article in Periodical
Magazine / Source Photochemical & Photobiological Sciences
MU Faculty or unit

Faculty of Science

Field Organic chemistry
Keywords Photochemistry; chiral auxiliary; benzoin; photoremovable protecting group
Description 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.
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