61275-22-7Relevant articles and documents
Straightforward Synthesis of Fluorinated Enals via Photocatalytic α-Perfluoroalkenylation of Aldehydes
Wulkesch, Christian,Czekelius, Constantin
, p. 7425 - 7438 (2021/06/21)
(Per)fluorinated substances represent an important compound class with regard to drug design and material chemistry. We found a mild, operationally simple, and inexpensive photocatalytic perfluoroalkenylation reaction giving tetrasubstituted, highly electron-deficient enals straight from aldehydes. This one-step reaction tolerates various functional groups and can be applied to a wide range of substrates giving the products in yields of 52-84%.
Mechanistic Studies on the Organocatalytic α-Chlorination of Aldehydes: The Role and Nature of Off-Cycle Intermediates
Ponath, Sebastian,Menger, Martina,Grothues, Lydia,Weber, Manuela,Lentz, Dieter,Strohmann, Carsten,Christmann, Mathias
supporting information, p. 11683 - 11687 (2018/09/10)
Herein we report the isolation and characterization of aminal intermediates in the organocatalytic α-chlorination of aldehydes. These species are stable covalent ternary adducts of the substrate, the catalyst and the chlorinating reagent. NMR-assisted kinetic studies and isotopic labeling experiments with the isolated intermediate did not support its involvement in downstream stereoselective processes as proposed by Blackmond. By tuning the reactivity of the chlorinating reagent, we were able to suppress the accumulation of rate-limiting off-cycle intermediates. As a result, an efficient and highly enantioselective catalytic system with a broad functional group tolerance was developed.
The preparation of (2r,5s)-2-t-butyl-3,5-dimethylimidazolidin-4-one
Graham, Thomas H.,Horning, Benjamin D.,MacMillan, David W. C.
, p. 42 - 53 (2014/04/03)
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