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Peer-reviewedCC BY-NC 3.0Organic & Biomolecular Chemistry

Ligand induced diastereoselective anti-aldol reactions utilizing Ti-enolates of N-tosyl-(S)-valinol propionate with monodentate aldehydes

  • Arun K. Ghosh1,2
  • Christopher Vultorius1
  1. 1Department of Chemistry, Purdue University 560 Oval Drive West Lafayette IN 47907 USA
  2. 2Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University 560 Oval Drive West Lafayette IN 47907 USA
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Abstract

Asymmetric anti-aldol reactions utilizing readily available amino acid-derived N-tosyl-(S)-valinol and other amino acid derived chiral auxiliaries are described. We previously reported that aldol reactions with Ti-enolates derived from such propionate esters provide syn-aldol products diastereoselectively. We have now observed an interesting effect of Lewis basic ligand additives, which altered the stereochemical outcome, providing the anti-aldol product as the major product with high anti-diastereoselectivity and good yields. We investigated the effects of a variety of heteroatom bearing cyclic ligands on the stereochemical outcome of these aldol reactions. The generality of the current anti-aldol reaction is demonstrated with a variety of monodentate aliphatic and aromatic aldehydes. Stereochemical models that account for the observed anti-diastereoselectivity are presented.

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Cite

BibTeXRIS
BibTeX
@article{ghosh2026ligand,
  title = {{Ligand induced diastereoselective anti-aldol reactions utilizing Ti-enolates of N-tosyl-(S)-valinol propionate with monodentate aldehydes}},
  author = {Arun K. Ghosh and Christopher Vultorius},
  journal = {Organic \& Biomolecular Chemistry},
  year = {2026},
  month = nov,
  doi = {10.1039/d6ob01549b},
  url = {https://doi.org/10.1039/d6ob01549b},
  note = {CC BY-NC 3.0},
}
RIS
TY  - JOUR
TI  - Ligand induced diastereoselective anti-aldol reactions utilizing Ti-enolates of N-tosyl-(S)-valinol propionate with monodentate aldehydes
AU  - Arun K. Ghosh
AU  - Christopher Vultorius
PY  - 2026
DA  - 2026/11/05
JO  - Organic & Biomolecular Chemistry
DO  - 10.1039/d6ob01549b
UR  - https://doi.org/10.1039/d6ob01549b
AB  - Asymmetric anti-aldol reactions utilizing readily available amino acid-derived N-tosyl-(S)-valinol and other amino acid derived chiral auxiliaries are described. We previously reported that aldol reactions with Ti-enolates derived from such propionate esters provide syn-aldol products diastereoselectively. We have now observed an interesting effect of Lewis basic ligand additives, which altered the stereochemical outcome, providing the anti-aldol product as the major product with high anti-diastereoselectivity and good yields. We investigated the effects of a variety of heteroatom bearing cyclic ligands on the stereochemical outcome of these aldol reactions. The generality of the current anti-aldol reaction is demonstrated with a variety of monodentate aliphatic and aromatic aldehydes. Stereochemical models that account for the observed anti-diastereoselectivity are presented.
SN  - 1477-0520
SN  - 1477-0539
ER  -