4.5 Review

Nitroenynes as Electrophiles in Organocatalysis and their Application in the Synthesis of Chiral Heterocycles

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 16, Pages 2255-2267

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100208

Keywords

Alkynes; Asymetric catalysis; Heterocycles; Nitrocompounds; Organocatalysis

Funding

  1. Agencia Estatal de Investigacion (AEI, Spanish Government)
  2. Fondo Europeo de Desarrollo Regional (FEDER, European Union) [CTQ2017-84900-P]
  3. Agencia Estatal de Investigacion (AEI, Spanish Government) [RYC-2016-20187]

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Nitroenynes have been recently utilized in organocatalysis, particularly in asymmetric catalysis. The review focuses on enantioselective Michael additions using nitroenynes as electrophiles, categorizing examples based on the nucleophile and providing mechanistic insights. Additionally, their applications in chiral heterocycles synthesis are also discussed.
Nitroenynes are a particular class of nitroalkenes, that have been recently used in organocatalysis. This review covers the recent examples in asymmetric catalysis using nitroenynes as electrophiles. The majority of the examples are enantioselective Michael additions, that have been categorized depending on the nucleophile, with representative examples providing insightful mechanistic details. Moreover, their applications to the synthesis of chiral heterocylces has also been discussed.

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