Photoremovable Chiral Auxiliary

• Authors: 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
• Web: http://pubs.rsc.org/en/Content/ArticleLanding/2012/PP/C1PP05096F
• Doi: http://dx.doi.org/10.1039/C1PP05096F
• 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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