Arun Guthikonda Lecture, Presented by Prof. Thorsten Bach, Technical University of Munich
Catalytic Photochemical Deracemization Reactions
Presented by Prof. Thorsten Bach
Hosted by Prof. Tom Rovis
Abstract:
Photochemistry enables an access to reaction pathways that are not viable in conventional transformations. The talk will revolve around the conversion of a racemic mixture to a single enantiomer in a catalytic photochemical deracemization reaction. 1,2 In an ideal scenario, quantitative yields of enantiomerically pure (>90% ee) compounds can be achieved in a single operation. The entropically disfavored and thermally impossible process is driven by light energy. Product classes which have been successfully deracemized include chiral allenes, olefins, cyclopropanes, and heterocyclic compounds. The reactions are catalyzed by a single photocatalyst which either acts by energy transfer 3 or by a reversible hydrogen atom transfer. 4 Possible applications, the underlying mechanistic considerations, and ongoing work on the topic will be presented.
- First report: A. Hölzl-Hobmeier, A. Bauer, A. V. Silva, S. M. Huber, C. Bannwarth, T. Bach;
Nature 2018, 564, 240. - Review: J. Großkopf, T. Bach; Angew. Chem. Int. Ed. 2023, 62, e202308241.
- For an example, see: T. Kratz, P. Steinbach, S. Breitenlechner, G. Storch, C. Bannwarth, T.
Bach; J. Am. Chem. Soc. 2022, 144, 10133. - For an example, see: J. Großkopf, M. Plaza, R. J. Kutta, P. Nuernberger, T. Bach, Angew.
Chem. Int. Ed. 2023, 62, e202313606.
Read more about the Bach Group here