Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 42, Pages 5853-5860Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800438
Keywords
Helicenes; Phosphines; Organocatalysis; Cyclization; Allenes; Enantioselectivity
Categories
Funding
- French Agence Nationale de la Recherche (ANR) [ANR-15-CE29-0012-01]
- IFCPAR/CEFIPRA [5505-2]
- Centre National de la Recherche Scientifique (CNRS)
- ICSN
- GDR Phosphore
- Agence Nationale de la Recherche (ANR) [ANR-15-CE29-0012] Funding Source: Agence Nationale de la Recherche (ANR)
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The use of phosphahelicenes as nucleophilic organocatalysts for [3+2] cyclization reactions between allenoates and 2-benzylidenemalononitriles has been extended by the systematic screening of phosphines with different helical scaffolds and substitution patterns. Among others, a new series of phosphahelicenes have been prepared by bromination/Suzuki coupling reactions of a pre-formed phosphahelicene. This late bromination approach represents a suitable strategy for accessing a broad variety of substituted phosphahelicenes from a single intermediate. It represents a powerful tool for the catalysis-oriented optimization of their structural features.
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