Photoremovable Chiral Auxiliary

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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
Citation
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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