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Peer-reviewedCC BY-NC-ND 4.0Dalton Transactions

Chiral phenoxyimino-amido aluminum complexes for the asymmetric cyanation of aldehydes

  • Jérémy Ternel
  • Francine Agbossou-Niedercorn
  • Régis M. Gauvin
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Abstract

The reactivity of triethylaluminum towards salicylaldimine sulfonamides was probed, affording well-defined complexes through consecutive protonolysis of two Al-C bonds by the proligand. These complexes, when combined with an achiral anilinic N-oxide, catalyze the asymmetric addition of trimethylsilylcyanide to a wide range of aldehydes, with good activity and enantioselectivity (up to 91% e.e.). Insertion of the benzaldehyde substrate into the Al-N amido bond was observed, bringing elements for discussion around the nature of the actual active species.

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Cite

BibTeXRIS
BibTeX
@article{ternel2026chiral,
  title = {{Chiral phenoxyimino-amido aluminum complexes for the asymmetric cyanation of aldehydes}},
  author = {Jérémy Ternel and Francine Agbossou-Niedercorn and Régis M. Gauvin},
  journal = {Dalton Transactions},
  year = {2026},
  month = oct,
  doi = {10.1039/c3dt53292e},
  url = {https://hal.science/hal-05772956v1},
  note = {CC BY-NC-ND 4.0},
}
RIS
TY  - JOUR
TI  - Chiral phenoxyimino-amido aluminum complexes for the asymmetric cyanation of aldehydes
AU  - Jérémy Ternel
AU  - Francine Agbossou-Niedercorn
AU  - Régis M. Gauvin
PY  - 2026
DA  - 2026/10/01
JO  - Dalton Transactions
DO  - 10.1039/c3dt53292e
UR  - https://hal.science/hal-05772956v1
AB  - The reactivity of triethylaluminum towards salicylaldimine sulfonamides was probed, affording well-defined complexes through consecutive protonolysis of two Al-C bonds by the proligand. These complexes, when combined with an achiral anilinic N-oxide, catalyze the asymmetric addition of trimethylsilylcyanide to a wide range of aldehydes, with good activity and enantioselectivity (up to 91% e.e.). Insertion of the benzaldehyde substrate into the Al-N amido bond was observed, bringing elements for discussion around the nature of the actual active species.
SN  - 1477-9226
SN  - 1477-9234
ER  -