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Issue 3, 2012
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Photoremovable chiral auxiliary

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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.

Graphical abstract: Photoremovable chiral auxiliary

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Publication details

The article was received on 15 Mar 2011, accepted on 29 Apr 2011 and first published on 23 Jun 2011


Article type: Paper
DOI: 10.1039/C1PP05096F
Citation: Photochem. Photobiol. Sci., 2012,11, 500-507
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    Photoremovable chiral auxiliary

    V. B. Kammath, P. Šebej, T. Slanina, Z. Kříž and P. Klán, Photochem. Photobiol. Sci., 2012, 11, 500
    DOI: 10.1039/C1PP05096F

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