A novel titanium/proline-derived catalyst system is reported for the enantioselective synthesis of <i>propargyl alcohols</i>. The reaction proceeded smoothly under mild conditions with efficient reaction times. Initially, lithium acetylide was employed to carry out the nucleophilic addition reaction, however poor reaction profile was achieved with poor enantioselectivities. When diethylzinc was used instead, high product yields (&gt;85%) and moderate to high enanitoselectivities were achieved (68-92%). Three different alkynes were used to carry out the reaction with a series of different aromatic and heterocyclic aldehydes. Better reaction profiles were achieved with aromatic alkynes than with aliphatic ones.

Titanium-proline derived system for the asymmetric synthesis of propargyl alcohols

254th National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.