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Photoracemization-Based Viedma Ripening of a BINOL Derivative.

Chemistry (Weinheim an der Bergstrasse, Germany) (2019-10-31)
Giuseppe Belletti, Carola Tortora, Indradevi D Mellema, Paul Tinnemans, Hugo Meekes, Floris P J T Rutjes, Svetlana B Tsogoeva, Elias Vlieg
ABSTRACT

Viedma ripening is a deracemization process that has been used to deracemize a range of chiral molecules. The method has two major requirements: the compound needs to crystallize as a conglomerate and it needs to be racemizable under the crystallization conditions. Although conglomerate formation can be induced in different ways, the number of racemization methods is still rather limited. To extend the scope of Viedma ripening, in the present research we applied UV-light-induced racemization in a Viedma ripening process, and report the successful deracemization of a BINOL derivative crystallizing as a conglomerate. Irradiation by UV light activates the target compound in combination with an organic base, required to promote the excited-state proton transfer (ESPT), leading thereafter to racemization. This offers a new tool towards the development of Viedma ripening processes, by using a cheap and "green" catalytic source like UV light to racemize suitable chiral compounds.

MATERIALS
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Product Description

Sigma-Aldrich
Benzyl bromide, reagent grade, 98%