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Updated: Jun 10, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Enantioselective Organozinc Addition to Aldehydes Using Planar Chiral [2.2]Paracyclophane-Imidazoline N,O-Ligands
Sundaravel Vivek Kumar1, Patrick J Guiry1
1Centre for Synthesis and Chemical Biology (CSCB), School of Chemistry, University College Dublin (UCD), Belfield, Dublin 4, Ireland.
Abstract:
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,SP)-UCD-Imphanol and (S,S,RP)-UCD-Imphanol, respectively.
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