Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 21, Pages 2923-2939Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100311
Keywords
Cyclohexadienones; Desymmetrization; Intramolecular hetero-Michael addition; Intramolecular Michael addition; Organocatalysis
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The organocatalytic enantioselective desymmetrization reaction via intramolecular (hetero)Michael addition is an effective strategy for creating complex carbo- and heterocycles with multiple stereocenters in a simple manner. The main challenge lies in the design and synthesis of the starting materials.
The organocatalytic enantioselective desymmetrization reaction by means of an intramolecular (hetero)Michael addition is a useful strategy for the creation of complex carbo- and heterocycles with the generation of multiple stereocenters in a very simple manner. The intramolecular addition of carbon, oxygen and nitrogen nucleophiles to prochiral substrates bearing electronically deficient olefins takes place in the presence of organocatalysts, such as chiral primary and secondary amines, NHCs, ureas, thioureas, and BINOL phosphoric acid derivatives, reaching high levels of diastereo- and enantioselectivity. The main bottleneck of this methodology is the design and synthesis of the starting materials, which compromises its application. To date, the majority of examples are related to the use of 1,4-cyclohexanedione derivatives.
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