Issue 3, 2012
From the journal:

Photochemical & Photobiological Sciences

Photoremovable chiral auxiliary†‡

Viju Balachandran Kammath,a   Peter Šebej,ab   Tomáš Slanina,a   Zdeněk Křížcd  and  Petr Klán*ab  

* Corresponding authors

a Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, Brno, Czech Republic
E-mail: klan@sci.muni.cz
Fax: +420-54949-2443
Tel: +420-54949-4856

b Research Centre for Toxic Compounds in the Environment, Faculty of Science, Masaryk University, Kamenice 3, Brno, Czech Republic

c National Centre for Biomolecular Research, Faculty of Science, Masaryk University, Kamenice 5, Brno, Czech Republic

d Central European Institute of Technology, Masaryk University, Kamenice 5, Brno, Czech Republic

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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Article information

DOI
https://doi.org/10.1039/C1PP05096F
Article type
Paper
Submitted
15 Mar 2011
Accepted
29 Apr 2011
First published
23 Jun 2011

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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