Issue 3, 2012

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.

Graphical abstract: Photoremovable chiral auxiliary

Supplementary files

Article information

Article type
Paper
Submitted
15 Mar 2011
Accepted
29 Apr 2011
First published
23 Jun 2011

Photochem. Photobiol. Sci., 2012,11, 500-507

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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