Synthesis of enantiopure C3-symmetric bulky trialkanolamines and their enantioselective inductivity during the alkynylation of aldehydes

•Ligands can be obtained in high yields (up to 90%) and regioselectivity up to 100%.•The enantioselectivity was higher with more bulky subustituent group presence.•Ligands gave up to 92% yield and 95% ee for the alkynylation of aldehydes.

Several C3-symmetric trialkanolamines can be efficiently obtained via molecular sieve-assisted epoxide ring opening with ammonia in high yields (up to 90%) and regioselectivity up to 100%. These trialkanolamines were effective for the asymmetric alkynylation of aldehydes and the propargyl alcohols were obtained in high yields (up to 92%) and high enantiomeric excesses (up to 95%). The 1H NMR spectra support that there could be a complex mixture of polynuclear Ti(IV)-based species form from the interaction of Ti(IV) with ligand.

Graphical abstractSeveral C3-symmetric trialkanolamines was very effective for the asymmetric alkynylation of aldehydes and the propargyl alcohols were obtained in high yields (up to 92%) and high enantiomeric excesses (up to 95%).Figure optionsDownload full-size imageDownload as PowerPoint slide