Enantioselective Photo-Organocatalysis:

Making Chiral Molecules with Light

Paolo Melchiorre^1,2

¹ICIQ – Institute of Chemical Research of Catalonia, Av. Països Catalans 16, 43007 (Tarragona, Spain);

²ICREA – Pg. Lluís Companys 23, 08010 (Barcelona, Spain)

e-mail: pmelchiorre@iciq.es

Light-driven processes considerably enrich the modern synthetic repertoire, offering a potent way to build complex organic frameworks.¹ In contrast, it is difficult to develop enantioselective catalytic photoreactions that can create chiral molecules with a well-defined three-dimensional arrangement.² Recently, our research laboratories³ has started a program aimed at translating the effective tools governing the success of ground state asymmetric organocatalysis into the realm of photochemical reactivity, exploiting the potential of key organocatalytic intermediates to directly participate in the photoexcitation of substrates. At the same time, the chiral organocatalyst can ensure effective stereochemical control. This single catalyst system, where stereoinduction and photoactivation merge in a sole organocatalyst, can serve for developing novel enantioselective photoreactions. The new synthetic possibilities, opened up by the application of organocatalysis within photochemical and radical patterns, will be discussed.⁴

1. Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176.

2. Brimioulle, R.; Lenhart, D.; Maturi, M. M.; Bach, T. Angew. Chem., Int. Ed. 2015, 54, 3872–3890.

3. (a) Arceo, E.; Jurberg, I. D.; Álvarez-Fernández, A.; Melchiorre, P. Nature Chem. 2013, 5, 750–756. (b) Woźniak, Ł.; Murphy, J. J.; Melchiorre, P. J. Am. Chem. Soc. 2015, 137, 5678–5681. (c) Murphy, J. J.; Bastida, D.; Paria, S.; Fagnoni, M.; Melchiorre, P. Nature 2016, 532, 218–222.

4. Research supported by the the Generalitat de Catalunya (CERCA Program), MINECO (Severo Ochoa Excellence Accreditation 2014-2018, SEV-2013-0319), and the European Research Council (ERC 681840 – CATA-LUX).