Enantioselective Organozinc Addition to Aldehydes Using Planar Chiral [2.2]Paracyclophane‐Imidazoline N,O‐Ligands
We present an improved and convenient synthesis of [2.2]paracyclophane-imidazoline N,O-ligands with central and planar chirality in seven steps starting from [2.2]paracyclophane. The utility of these ligands in organozinc additions to aldehydes is described. The asymmetric ethylation of aldehydes proceeded with enantioselectivities of up to 97 % ee, while the asymmetric arylation of aldehydes gave up to 95 % ee (R) and 82 % ee (S) using (S,S,S<sub>P</sub>)-UCD-Imphanol and (S,S,R<sub>P</sub>)-UCD-Imphanol, respectively.
Authors
- Patrick J. Guiry (ORCID: https://orcid.org/0000-0002-2612-8569)
- Sundaravel Vivek Kumar (ORCID: https://orcid.org/0000-0002-8054-730X)
Institutions
- University College Dublin (IE)
- National University of Ireland (IE)
Publication Details
- Journal
- Chemistry - A European Journal
- Published
- 2024-10-14
- DOI
- https://doi.org/10.1002/chem.202403345
- Citations
- 6
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 1.50
Funders
- Science Foundation Ireland
- Irish Research Council