title: Inverse temperature dependence in the diastereoselective addition of Grignard reagents to a tetrahydrofurfural.
abstract: A remarkable example of inverse-temperature-dependent diastereoselectivity was uncovered while investigating the addition of Grignard reagents to a 3-hydroxytetrahydrofurfural. The free hydroxyl group in the tetrahydrofurfural was found to play a key role in these processes, a result corroborated through a series of DFT calculations that also highlighted an entropic preference for the formation of one diastereomer.
authors.affiliation: Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC, Canada V5S 1S6.
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Mowat
authors.forename: Baldip
authors.initials: B
authors.lastname: Kang
authors.forename: Branden
authors.initials: B
authors.lastname: Fonovic
authors.forename: Travis
authors.initials: T
authors.lastname: Dudding
authors.forename: Robert
authors.initials: R
authors.lastname: Britton