457612-06-5Relevant academic research and scientific papers
Clean and easy photochemistry
Ciana, Claire-Lise,Bochet, Christian G.
, p. 650 - 654 (2008/03/11)
In this paper we try to convince you that the usual prejudices against photochemistry are not always well founded, supported by examples from the literature and from our own work. In fact, photochemistry can be a very powerful tool, for example in some elegant total syntheses which use key photochemical steps. Furthermore, the exploitation of chromatic orthogonality which allows wavelength-selective reactions, and recent strategies opening the possibility of enantioselective catalysis in photochemical reactions, expand the scope of this versatile synthetic tool. Finally, state-of-art LED-technology has allowed the development of small and easy-to-use photoreactors. Schweizerische Chemische Gesellschaft.
Wavelength-controlled orthogonal photolysis of protecting groups
Blanc, Aurelien,Bochet, Christian G.
, p. 5567 - 5577 (2007/10/03)
The selective control of a chemical process by the use of an electromagnetic wave has been a challenging goal for several decades. In this article, we describe for the first time the use of a monochromatic light beam to differentiate two different reactive centers. A direct application of this concept is found in the chemistry of protecting groups. Two different photolabile protecting groups were tuned to be responsive to a specific wavelength (e.g., 254 or 420 nm). Using derivatives of the 2-nitroveratryl fragment (such as 10, sensitive at 420 nm) and 3′,5′-dimethoxybenzoin fragment (such as 4, sensitive at 254 nm), it was shown that energy transfer phenomena did not erode the selectivity. Both the inter- and the intramolecular cases were studied and showed selectivities within the synthetically useful range. Hence, we could replace the traditional chemical orthogonality by a chromatic orthogonality.
